- Lithium Perchlorate Mediated Three-Component Preparation of α-Aminonitriles under Solvent-Free Conditions
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A three-component reaction between aliphatic or aromatic aldehyde, an amine and trimethylsilyl cyanide mediated by solid LiClO4, gave amino nitriles in good to excellent yields. The reaction proceeded smoothly under solvent-free conditions without any side products.
- Azizi, Najmedin,Saidi, Mohammad R.
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- Silica sulfuric acid catalyzed one-pot synthesis of α-aminonitriles
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A simple and efficient method has been developed for the synthesis of α-aminonitriles by a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide in the presence of a catalytic amount of silica sulfuric acid at room temperature. The silica sulfuric acid is reusable and could be applied in subsequent reactions with comparable activity. Georg Thieme Verlag Stuttgart.
- Chen, Wei-Yi,Lu, Jun
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- Magnetically separable g-C3N4 hybrid nanocomposite: Highly efficient and eco-friendly recyclable catalyst for one-pot synthesis of α-aminonitriles
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A magnetically separable graphitic carbon nitride nanocomposite (Fe3O4/g-C3N4) as a catalyst for the three-component condensation reactions of carbonyl compounds, amines and trimethylsilylcyanide was thoroughly investigated. The reaction of these three components was found to be efficient, economical and green and took place in the presence of a catalytic amount of the magnetically separable catalyst to yield the corresponding α-aminonitriles in good to excellent yields. The prepared nanocomposite was characterized using scanning electron microscopy and energy-dispersive X-ray and Fourier transform infrared spectroscopies. The nanocomposite was also found to be reusable could be recovered easily and reused several times without distinct deterioration in its catalytic activity.
- Azizi, Najmedin,Farhadi, Elham
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- RuCl3 catalyzed one-pot synthesis of α-aminonitriles
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A simple and efficient method was developed for the synthesis of α-aminonitriles by simply mixing aldehydes, amines, and trimethylsilyl cyanides in the presence of a catalytic amount of RuCl3 at room temperature.
- De, Surya Kanta
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Read Online
- Synthesis of α-aminonitriles using silica-bonded N-propylpiperazine sulfamic acid as a recyclable catalyst
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α-Aminonitriles were synthesized via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide using silica-bonded N-propylpiperazine sulfamic acid (SBPPSA) as a recyclable solid acid at room temperature. SBPPSA showed much the same efficiency when used in consecutive reaction runs.
- Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
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Read Online
- Copper-vitamin B6 coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α-aminonitriles from benzyl alcohols
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A novel and effective dual catalysis system, copper combined with pyridoxal phosphate, which is anchored in maghemite nanoparticles were designed and applied to synthesize α-aminonitriles from benzyl alcohols. This catalytic system has the potential ability to perform oxidation reactions and subsequently synthesize alpha-amino nitrile in a reaction environment. Thus, the purpose of this paper is introducing a heterogeneous, sustainable and recyclable catalytic system to perform reactions that require a transition metal catalyst and organocatalyst continuously to achieve a target molecule. The catalysis system is examined and investigated with seven useful analyses such as FT-IR, TGA, VSM, SEM, TEM, XRD, and ICP.
- Esfandiary, Naghmeh,Nakisa, Athar,Radfar, Iman,Azizi, Kobra,Mehraban, Jamshid Azarnia,Heydari, Akbar
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Read Online
- A carbon dioxide-promoted three-component Strecker reaction
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A three-component Strecker reaction of aldehydes, amines and KCN has been performed for the first time in supercritical carbon dioxide. In the proposed procedure, non-toxic and non-flammable carbon dioxide acts not only as an environmentally benign reaction medium but also as a reaction promoter via in situ formation of carbonic acid which provides a gradual release of the true cyanating agent (HCN) from available KCN. The reaction conditions (pressure, temperature, and concentrations of reagents) were optimized, and various aromatic and aliphatic amines and aldehydes were transformed into valuable α-amino nitriles including prospective pharmacological substances. The equimolar amount of used cyanogen reagent, carrying out the process in a sealed autoclave in a 'green' solvent medium under mild conditions (90 bar, 35 °C) along with the high yields of products and the scalability of the developed procedure make it suitable for sustainable industrial applications. This journal is
- Fauziev, Ruslan V.,Ivanov, Roman E.,Kuchurov, Ilya V.,Zlotin, Sergei G.
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p. 10137 - 10144
(2021/12/24)
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- Strecker reactions with hexacyanoferrates as non-toxic cyanide sources
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The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.
- Grundke, Caroline,Opatz, Till
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supporting information
p. 2362 - 2366
(2019/05/17)
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- A unique combination of KI/ZnFe2O4 as a catalyst for oxidative Strecker reaction
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α-Aminonitriles as key intermediates for the preparation of α-amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert-butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products. Operational simplicity, short reaction time and recyclability of the catalyst are advantages of this protocol.
- Ghandi, Leila,Kazemi Miraki, Maryam,Karimi, Meghdad,Radfar, Iman,Heydari, Akbar
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- Efficient synthesis of α-aminonitriles over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H), as a reusable acid catalyst
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Abstract: Good to excellent yields of α-aminonitriles are achieved through three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H). The advantages of this protocol include: simplicity, short reaction time, high yields, ease of product isolation and reusability of the catalyst. Graphical abstract: MSNs-HPZ-SO3H is prepared as an acid catalyst and successfully used for three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides (TMSCN) under solvent-free conditions, a straightforward strategy for the synthesis of α-aminonitriles.[Figure not available: see fulltext.].
- Nasresfahani, Zahra,Kassaee, Mohamad Z.,Eidi, Esmaiel
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p. 1819 - 1825
(2019/04/17)
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- Expeditious and efficient synthesis of Strecker's α-aminonitriles catalyzed by sulfated polyborate
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A straightforward, mild, efficient, and environmentally benign protocol for a three-component Strecker reaction of aldehydes or ketones, amines, and trimethylsilyl cyanide catalyzed by sulfated polyborate has been described to afford α-aminonitriles under solvent-free reaction conditions. The major advantages of the present method are excellent yields, shorter reaction time, simple experimental procedure, easy workup procedure, recyclability of the catalyst, solvent-free reaction conditions and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
- Indalkar, Krishna S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
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supporting information
p. 2144 - 2148
(2017/05/10)
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- Synthesis of novel magnetic nanoparticles with urea or urethane moieties: Applications as catalysts in the Strecker synthesis of α-aminonitriles
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Four novel magnetic nanoparticle catalysts with urea or urethane moieties are reported. The silica-coated magnetic nanoparticles were simply functionalized via addition of 3-(triethoxysilyl)propylisocyanate (TESPIC), amine or amino alcohol. TESPIC with dual labile functional groups was used as a suitable precursor for the synthesis of urethane-based catalysts. The newly synthesized catalysts were fully characterized using a variety of techniques. These functionalized magnetic nanoparticles were used as reusable catalysts in the Strecker synthesis of α-aminonitrile derivatives under solvent-free conditions at 50?°C.
- Baghery, Saeed,Zolfigol, Mohammad Ali,Schirhagl, Romana,Hasani, Masoumeh,Stuart, Marc C.A.,Nagl, Andreas
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- A catalytic, one-pot and green synthesis of a-amino nitriles: Cu(BF4)2.x H2O an efficient catalyst
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The Strecker reaction is a first reported multicomponent reaction for the preparation of a-aminonitriles. The a-aminonitriles are important intermediates for various aminoacids, 1,2-diazines, heterocycles and biologically active compounds like Saframycin A and Ecteinascidin 746. The preparation of a-aminonitriles by Strecker approach using MCR attracted many research groups owing atom economy to avoid multistep synthesis and to follow Green chemistry principles. Methods: A-aminonitriles have been synthesized using Strecker reaction by treatment of aldehydes, amines, with TMSCN in the presence of Cu(BF4)2.xH2O as a catalyst in one pot under neat conditions. Various aromatic and aliphatic aldehydes have been studied with different primary and secondary amines. Results: The reaction condition has been optimized by choosing a model reaction under various solvents and found good yields under neat conditions. Moreover, various catalytic amounts of Cu(BF4)2.xH2O has also been studied and found 3 mole% providing better yields. The reaction has been studied with different substrates of aldehydes and amines. Some of the products were characterized by comparison of their spectral data (1H NMR, 13C NMR, IR and MS) and physical properties with those of authentic samples reported in the literature. Conclusion: Afacile and efficient one-pot synthesis of a-amino nitriles at ambient temperature using copper(II)tetrafluoroborate as a novel catalyst under solvent-free conditions via Strecker reaction is reported. The process is simple and environmentally benign using the commercially available and inexpensive catalyst.
- Tadiparthi, Krishnaji,Raghavendra,Kamal, Ahmed
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supporting information
p. 440 - 445
(2017/07/24)
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- Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions
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A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
- Hernández, José G.,Turberg, Mathias,Schiffers, Ingo,Bolm, Carsten
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supporting information
p. 14513 - 14517
(2016/10/03)
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- Magnetic Fe3O4-BF3: Highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles
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Fe3O4 magnetic nanoparticle-supported BF3 was prepared as a new magnetically separable Lewis acid catalyst and successfully used for the one-pot synthesis of α-aminonitriles. A broad range of substrates including the aromatic and heteroaromatic aldehydes, cyclic ketones (cyclopentanone, cyclohexanone and cycloheptanone), aryl-alkyl ketones, diaryl ketones and tetralones, isatin derivatives and acenaphthenequinone were condensed with amines (aliphatic and aromatic) and trimethylsilyl cyanide. All reactions were completed in short times and products were obtained in good to excellent yields. The catalyst could be recycled and reused several times without any loss of efficiency. Finally, α-aminonitrile containing adenine was successfully synthesized.
- Shekouhy, Mohsen,Moaddeli, Ali,Khalafi-Nezhad, Ali
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p. 3805 - 3827
(2016/04/05)
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- Propylphosphonic anhydride (T3P) catalyzed one-pot synthesis of α-aminonitriles
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Abstract The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.
- Reddy, Sirigireddy Sudharsan,Reddy, Bhoomireddy Rajendra Prasad,Reddy, Peddiahgari Vasu Govardhana
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p. 739 - 743
(2015/08/03)
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- Synergistic effect of a bis(proazaphosphatrane) in mild palladium-catalyzed direct α-arylations of nitriles with aryl chlorides
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The effect of a bis(proazaphosphatrane) ligand on the palladium-catalyzed direct α-arylation of nitriles with various aryl chlorides under mild conditions is reported. Comparisons of the catalytic properties of this ligand with those of three related mono(proazaphosphatrane)s under the same reaction conditions revealed that bis(proazaphosphatrane) displayed a synergistically enhanced activity. In the presence of the bis(proazaphosphatrane) ligand, ethyl cyanoacetate and primary as well as secondary nitriles were efficiently coupled with a wide variety of aryl chlorides that contained electron-rich, electron-poor, and electron-neutral groups.
- Han Kim, So,Jang, Wonseok,Kim, Min,Verkade, John G.,Kim, Youngjo
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p. 6025 - 6029
(2015/03/30)
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- Magnetic solid sulfonic acid decorated with hydrophobic regulators: A combinatorial and magnetically separable catalyst for the synthesis of α-aminonitriles
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A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of α-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O 4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.
- Mobaraki, Akbar,Movassagh, Barahman,Karimi, Babak
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supporting information
p. 352 - 358
(2014/08/05)
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- Zn(OAc)2·2H2O-catalyzed one-pot efficient synthesis of α-amino nitriles
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A mild, efficient one-pot three component strecker reaction involving electronically and structurally divergent aldehydes, amines and trimethly silyl cyanide in chloroform as solvent at room temperature was accomplished in moderate to excellent yields using an inexpensive and readily available catalyst, Zn(OAc)2.2H2O.
- Reddy, V. Venkata Rami,Saritha,Ramu,Varala, Ravi,Jayashree
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p. 7439 - 7442
(2015/04/22)
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- Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine
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Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright
- Barnett, Derek W.,Refaei, Maryanne S.,Curley Jr., Robert W.
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- Silica boron sulfuric acid nanoparticles: As an efficient and reusable catalyst for the large-scale synthesis of α-amino nitriles using the strecker reaction
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A highly efficient and green procedure for the large-scale synthesis of α-amino nitriles using three-component condensation of carbonyl compounds, amines, and trimethylsilylcyanide has been developed. Silica boron sulfuric acid nanoparticles (SBSANs) are found as an efficient heterogeneous catalyst for the promotion of this process at room temperature under solvent-free conditions. This protocol offers an effective and scale-up procedure for the synthesis of various α-amino nitriles using a wide range of amines and carbonyl compounds in relatively short reaction time with the excellent isolated yields. In addition, the SBSAN catalyst is easily separated from the reaction mixture by simple filtration and can be reused several times.
- Khalafi-Nezhad, Ali,Foroughi, Habib Ollah,Panahi, Farhad
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- Zinc triflate a water compatible, green catalyst in one pot three-component efficient synthesis of α-Amino nitriles
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α-Amino nitriles are synthesized in one pot three-component coupling of aldehydes, amines and trimethylsilyl cyanide using catalytic amount of zinc triflate at ambient temperature.
- Suresh,Chand, Subhash,Sandhu, Jagir S.
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p. 853 - 856
(2013/08/23)
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- Dehydroascorbic acid (DHAA) capped magnetite nanoparticles as an efficient magnetic organocatalyst for the one-pot synthesis of α-aminonitriles and α-aminophosphonates This article is dedicated to memory of Majid Shahriari
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A dehydroascorbic acid capped magnetite (DHAA-Fe3O4) catalyst is prepared and used for the one-pot synthesis of α-aminonitriles and α-aminophosphonates. Different derivatives of these compounds are synthesized in good yields.
- Saberi, Dariush,Cheraghi, Samaneh,Mahdudi, Samaneh,Akbari, Jafar,Heydari, Akbar
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p. 6403 - 6406
(2013/11/19)
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- L-Proline catalyzed one pot synthesis of α-aminonitriles
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l-Proline (20 mol %) was found to be an efficient organocatalyst for one pot synthesis of a variety of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide (TMSCN) in acetonitrile at ambient temperature giving good to excellent yields (72-95%).
- Nasreen, Aayesha
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p. 3797 - 3800
(2013/07/05)
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- Nafion-Fe: A new efficient "green" lewis acid catalyst for the ketonic strecker reaction
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The synthesis of various α-aminonitriles, precursors of α-amino acids has been carried out in moderate to high yields and high purity by the Strecker reaction from ketones, aliphatic/aromatic amines and TMSCN using a new "green" Lewis acid catalyst, Nafion-Fe (iron Nafionate, Fe(III) salt of Nafion-H, a solid polymeric perfluoroalkanesulfonic acid) under conventional thermal as well as microwave conditions. Microwave and solvent-free conditions applied in this method shorten the reaction times, improve the yields and diminishes the formation of side products. Strecker reaction occurs smoothly with secondary aliphatic amines also under these conditions which is not common under conventional conditions.
- Surya Prakash,Bychinskaya, Inessa,Marinez, Eric R.,Mathew, Thomas,Olah, George A.
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p. 303 - 312
(2013/05/09)
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- Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: A facile access to α-methylene γ-lactams
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The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams. The Royal Society of Chemistry 2012.
- Pan, Feng,Chen, Jian-Ming,Zhuang, Zhe,Fang, Yin-Zhi,Zhang, Sean Xiao-An,Liao, Wei-Wei
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p. 2214 - 2217
(2012/04/10)
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- Catalyst-free, facile, and an efficient synthesis of α-aminonitriles employing Zn(CN)2 as an ecofriendly cyanating agent
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An efficient and eco-friendly method has been developed for the synthesis of α-aminonitriles via one-pot three-component condensation of carbonyl compounds, amines, and Zn(CN)2 under mild conditions. This protocol has the features of use of inexpensive, ecofriendly readily available, effective cyanide source, high yield, and simple work-up procedure.
- Shah, Sakshi,Singh, Baldev
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experimental part
p. 151 - 156
(2012/01/19)
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- Silica-bonded N-propyl diethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of α-aminonitriles
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Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
- Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
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p. 1095 - 1100
(2013/01/14)
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- Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
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Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
- Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
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p. 1095 - 1100
(2015/06/30)
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- Sulfated tungstate: A green catalyst for Strecker reaction
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A straightforward, mild, efficient, and general method has been developed for the synthesis of α-aminonitriles via Strecker reaction starting from aldehydes or ketones, amines, and trimethylsilyl cyanide in the presence of sulfated tungstate as a heterogeneous mild solid acid catalyst at room temperature and solvent free condition. The developed method has been successfully applied for the synthesis of a wide range of α-aminonitriles with variable functionality.
- Pathare, Sagar P.,Akamanchi, Krishnacharya G.
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experimental part
p. 871 - 875
(2012/03/08)
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- Modified asymmetric strecker reaction of aldehyde with secondary amine: A protocol for the synthesis of S-clopidogrel (an antiplatelet agent)
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A first approach for catalytic asymmetric Strecker reaction of aldehydes with a secondary amine in the presence of sodium fluoride using hydroquinine as chiral catalyst was developed. The catalytic system gave α-aminonitriles in excellent yields (up to 95
- Sadhukhan, Arghya,Saravanan,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
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supporting information; experimental part
p. 7076 - 7080
(2012/11/07)
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- Catalyst-free Strecker reaction in water: A simple and efficient protocol using acetone cyanohydrin as cyanide source
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A simple, convenient, and practical method for the synthesis of α-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported. Copyright
- Galletti, Paola,Pori, Matteo,Giacomini, Daria
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experimental part
p. 3896 - 3903
(2011/09/12)
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- Heterogeneously catalysed Strecker-type reactions using supported Co(ii) catalysts: Microwave vs. conventional heating
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A range of α-aminonitriles could be efficiently prepared from various aldehydes/ketones and primary or secondary amines using a highly active and stable Co(ii) complex supported on different mesoporous supports at both room temperature and low temperature microwave irradiation under solventless conditions. Catalysts were also highly reusable under the investigated reaction conditions and could be reused at least 10 times without loss of catalytic activity. The Royal Society of Chemistry.
- Rajabi, Fatemeh,Nourian, Saghar,Ghiassian, Sara,Balu, Alina M.,Saidi, Mohammad Reza,Serrano-Ruiz, Juan Carlos,Luque, Rafael
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supporting information; experimental part
p. 3282 - 3289
(2011/12/15)
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- Oxalic acid as a simple and efficient organocatalyst for three-component synthesis of α-amino nitriles
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A simple, efficient, and general method has been developed for the synthesis of α-amino nitriles. Oxalic acid as a Br?nsted acid promotes the addition of TMSCN to various imines (generated in situ).
- Vahdat, Seyed Mohammad,Khaksar, Samad,Khavarpour, Maryam
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experimental part
p. 543 - 546
(2012/01/14)
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- Ga-TUD-1: A new heterogeneous mesoporous catalyst for the solventless expeditious synthesis of α-aminonitriles
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The high surface area three-dimensional porous catalyst has been prepared and characterized by TEM, BET S.A, low angle XRD, 29Si MAS NMR, NH3 TPD techniques. A simple, efficient and rapid method for the green synthesis of α-aminonitriles has been demonstrated over a new mesoporous gallosilicate catalyst Ga-TUD-1. The solventless technique has been applied for the synthesis of a range of compounds with variable functionality with excellent yield and selectivity. The catalyst has been recycled four times with reproducible yield.
- Karmakar, Bikash,Sinhamahapatra, Apurba,Panda, Asit Baran,Banerji, Julie,Chowdhury, Biswajit
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experimental part
p. 111 - 117
(2011/10/13)
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- Preparation of silica-based ionic liquid an efficient and recyclable catalyst for one-pot synthesis of α-aminonitriles
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Preparation of N-(3-silicapropyl) imidazolium hydrogen sulfate ([Sipim]HSO4) as a heterogeneous acidic ionic liquid is described. This heterogeneous ionic liquid was used as catalyst for the synthesis of α-aminonitriles by a one-pot condensation of aldehydes, amines, and trimethylsilyl cyanide at room temperature. Catalyst could be recycled for several times without any additional treatment. Graphical Abstract: A simple and efficient procedure for the preparation of silica-based acidic ionic liquid ([Sipim]HSO4) is described. This heterogeneous solid acid is employed as a catalyst for the synthesis of a-amino nitriles at room temperature. [Figure not available: see fulltext.]
- Nouri Sefat, Maryam,Saberi, Dariush,Niknam, Khodabakhsh
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experimental part
p. 1713 - 1720
(2012/03/11)
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- Efficient Co(ii) heterogeneously catalysed synthesis of α-aminonitriles at room temperature via Strecker-type reactions
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An environmentally friendly and highly active mesoporous Co(ii) complex on mesoporous SBA-15 material could be used as an easily recoverable catalyst for the synthesis of α-aminonitriles from a wide range of aldehydes/ketones and primary or secondary amines with good to excellent conversions yields at room temperature under solventless conditions. The catalyst can be recovered by simple filtration and could be reused at least 10 times without loss of catalytic activity.
- Rajabi, Fatemeh,Ghiassian, Sara,Saidi, Mohammad Reza
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supporting information; experimental part
p. 1349 - 1352
(2010/09/15)
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- KSF-supported heteropoly acids catalyzed one-pot synthesis of α-aminonitriles
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In. the presence of KSF-supported heteropoly acid as a heterogeneous, reusable and inexpensive catalyst, three-component reactions between aldehydes or ketones, amines, and trimethylsilyl cyanide preceded to afford a-aminonitriles in excellent yields, very short reaction times, and low loading of catalyst. This catalyst was highly selective and other functional groups including carbon-carbon double bond, and heterocyclic moieties did not affect the reaction.
- Rafiee, Ezzat,Rashidzadeh, Solmaz,Eavani, Sara,Joshaghani, Mohammad
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experimental part
p. 209 - 215
(2011/11/29)
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- Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the three-component synthesis of α-amino nitriles
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Silica-bonded S-sulfonic acid (SBSSA) is employed as a recyclable catalyst for the synthesis of α-amino nitriles. These syntheses were performed via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide under mild reaction conditions at room temperature.
- Niknam, Khodabakhsh,Saberi, Dariush,Sefat, Maryam Nouri
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experimental part
p. 2959 - 2962
(2010/06/21)
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- Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates
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Trifluoroethanol is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of aldehydes or ketones, amines and trimethylsilyl cyanide or trimethyl phosphite to afford the corresponding α-amino nitriles or α-amino phosphonates in high yields. This protocol does not require the use of an acid or base catalyst.
- Heydari, Akbar,Khaksar, Samad,Tajbakhsh, Mahmood
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body text
p. 77 - 80
(2009/04/14)
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- Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles
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Superparamagnetic Fe3O4 is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of α-aminonitriles from aldehydes, amines, and TMSCN. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained rapidly at room temperature in good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture.
- Mojtahedi, Mohammad M.,Saeed Abaee,Alishiri, Tooba
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experimental part
p. 2322 - 2325
(2009/09/06)
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- CuSO4.5H2O catalyzed efficient one pot synthesis of α-amino nitriles
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α-Amino nitriles are synthesized in a one pot three component coupling of aldehydes, amines and trimethylsilyl cyanide using catalytic amount of CuSO4.5H2O at ambient temperature.
- Suresh, Anil Saini,Sandhu, Jagir S.
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experimental part
p. 261 - 264
(2010/04/05)
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- γ-Al2O3-supported 12-tungstosilicic acid as an efficient heterogeneous catalyst for the synthesis of α-aminonitrile
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The multicomponent Strecker reaction using trimethylsilyle cyanide was performed in very short reaction times, and α-aminonitriles were prepared in excellent yields in the presence of a catalytic amount of alumina-supported tungstosilicic acid. Copyright Taylor & Francis Group, LLC.
- Rafiee, Ezzat,Rashidzadeh, Solmaz,Joshaghani, Mohammad,Chalabeh, Hadi,Afza, Kambiz
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experimental part
p. 2741 - 2747
(2009/04/05)
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- LiBr: A mild Lewis acid catalyst for efficient one-pot synthesis of α-amino nitriles
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α-Amino nitriles are synthesized in a one-pot, three-component coupling of aldehydes, amines, and trimethylsilyl cyanide using a catalytic amount of LiBr at ambient temperature. Copyright Taylor & Francis Group, LLC.
- Suresh, Anil Saini,Sandhu, Jagir S.
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p. 3655 - 3661
(2008/12/23)
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- Indium(III) iodide-mediated Strecker reaction in water: an efficient and environmentally friendly approach for the synthesis of α-aminonitrile via a three-component condensation
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A mild, efficient and environmentally friendly method has been developed for the synthesis of α-aminonitriles via a three-component condensation of aldehyde, amine and TMSCN in the presence of a catalytic amount of indium(III) iodide in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding products in moderate to excellent yields.
- Shen, Zhi-Liang,Ji, Shun-Jun,Loh, Teck-Peng
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p. 8159 - 8163
(2008/12/21)
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- K5CoW12O40·3H2O: Heterogeneous catalyst for the strecker-type aminative cyanation of aldehydes and ketones
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One-step synthesis of α-aminonitriles was successfully carried out by a three-component condensation of aldehydes or ketones, amines, and potassium cyanide in the presence of a catalytic amount of K5CoW12O40·3H2O as an efficient, reusable, and nontoxic catalyst. Copyright Taylor & Francis Group, LLC.
- Rafiee, Ezzat,Azad, Alireza
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p. 1127 - 1132
(2008/02/01)
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- Lithium tetrafluoroborate-catalyzed solventless synthesis of α-aminonitriles
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Lithium tetrafluoroborate-catalyzed one-pot, highly efficient, and solvent-free protocol has been developed for the synthesis of α-aminonitriles from aldehydes/ketones, amines, and trimethylsilyl cyanide.
- Desai, Uday V.,Mitragotri, Satish D.,Thopate, Takaram S.,Pore, Dattaprasad M.,Wadgaonkar, Prakash P.
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p. 759 - 762
(2008/02/09)
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- One-pot three-component synthesis of α-amino nitriles catalyzed by 2,4,6-trichloro-1,3,5-triazine (cyanuric acid)
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A simple and efficient method has been developed for the synthesis of α-amino nitriles from aldehydes, amines and trimethylsilyl cyanide (Me3SiCN) in the presence of a catalytic amount of cyanuric acid at room temperature.
- Das, Biswanath,Kumar, Rathod Aravind,Thirupathi, Ponnaboina
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p. 1206 - 1210
(2008/03/12)
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- Sulfamic acid catalyzed direct condensation of aldehydes, amines, and TMSCN to α-aminonitriles at ambient temperature
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A simple and efficient method has been developed for the synthesis of α-aminonitriles by a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide in the presence of a catalytic amount of sulfamic acid at room temperature. Georg Thieme Verlag Stuttgart.
- Li, Zhenjiang,Sun, Yingjie,Ren, Xinghua,Wei, Ping,Shi, Yuhu,Ouyang, Pingkai
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p. 803 - 805
(2007/12/25)
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- Cerium(III) chloride: A highly efficient reagent for the synthesis of α-aminonitriles
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We report a highly efficient, one-pot, three-component condensation of carbonyl compounds, amines, and TMSCN in MeCN; the reaction is significantly promoted by the catalytic amount of cerium(III) chloride at ambient temperature in excellent yields without any adverse effect on the other substituents. The method afforded an elegant alternative to the synthesis of α- aminonitriles. The reactions are fast and clean, and the products obtained are of high purity. Copyright Taylor & Francis Group, LLC.
- Pasha,Nanjundaswamy,Jayashankara
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p. 4371 - 4380
(2008/03/13)
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- [HP(HNCH2CH2)3N]NO3: An efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions
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In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of α-amino and α-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion.
- Fetterly, Brandon M.,Jana, Nirmal K.,Verkade, John G.
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p. 440 - 456
(2007/10/03)
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- (Bromodimethyl)sulfonium bromide catalyzed one-pot synthesis of α-aminonitriles
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A novel, simple and efficient one-pot synthesis of α-aminonitriles has been achieved by a three-component condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of (bromodimethyl)sulfonium bromide as a catalyst at room temperature. The products were obtained in high yields and in short reaction times. Georg Thieme Verlag Stuttgart.
- Das, Biswanath,Ramu,Ravikanth,Reddy, K. Ravinder
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p. 1419 - 1422
(2007/10/03)
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- Photochemical generation of highly destabilized vinyl cations: The effects of α- and β-trifluoromethyl versus α- and β-methyl substituents
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(Chemical Equation Presented). The photochemical reactions in methanol of the vinylic halides 1-4, halostyrenes with a methyl or a trifluoromethyl substituent at the α- or β-position, have been investigated quantitatively. Next to E/Z isomerization, the reactions are formation of vinyl radicals, leading to reductive dehalogenation products, and formation of vinyl cations, leading to elimination, nucleophilic substitution, and rearrangement products. The vinyl cations are parts of tight ion pairs with halide as the counterion. The elimination products are the result of β-proton loss from the primarily generated α-CH3 and α-CF3 vinyl cations, or from the α-CH3 vinyl cation formed from the β-CH3 vinyl cation via a 1,2-phenyl shift. The β-CF 3 vinyl cation reacts with methanol yielding nucleophilic substitution products, no migration of the phenyl ring producing the α-CF3 vinyl cation occurs. The α-CF3 vinyl cation, which is the most destabilized vinyl cation generated thus far, gives a 1,2-fluorine shift in competition with proton loss. The experimentally derived order of stabilization of the vinyl cations photogenerated in this study, α-CF3 3 3 3, is corroborated by quantum chemical calculations, provided the effect of solvent is taken into account.
- Van Alem, Kaj,Belder, Geerte,Lodder, Gerrit,Zuilhof, Han
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p. 179 - 190
(2007/10/03)
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