- Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes
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Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.
- Liu, Richard Y.,Bae, Minwoo,Buchwald, Stephen L.
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Read Online
- Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine
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Four new fluorescent dyes derived from the 3H-benzo[a]pyrazolo[3,4-j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated and the results revealed that, in some cases, they have higher quantum yields compared with well-known fluorescent dyes such as fluorescein. Solvent effects on the fluorescence characteristics of the four compounds indicated that the emission wavelength is red-shifted with increasing solvent polarity. Furthermore, density functional theory calculations using the B3LYP hybrid functional and the 6-311++G(d,p) basis set provided the optimised geometries and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained using the time-dependent density functional theory method.
- Alipoor, Hamideh,Pordel, Mehdi,Morsali, Ali
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Read Online
- Straightforward conversion of alcohols into nitriles
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The reaction of various alcohols with cyanogen bromide, triphenylphosphine, and a base afforded the corresponding nitrile in satisfactory yields. Copyright
- Tarrade-Matha, Aurelie,Pillon, Florence,Doris, Eric
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Read Online
- Mild and reversible dehydration of primary amides with PdCl2 in aqueous acetonitrile
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(Chemical Equation Presented) A new, mild, and reversible method to convert primary amides to nitriles in good yields using PdCl2 in aqueous acetonitrile is described.
- Maffioli, Sonia I.,Marzorati, Ettore,Marazzi, Alessandra
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Read Online
- Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters
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The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.
- Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong
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- Method for dehydrating primary amide into nitriles under catalysis of cobalt
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The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.
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Paragraph 0078-0080
(2021/06/21)
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- Preparation method of naphthalene ring C marked α .
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The invention discloses C labeled α - naphthalene acetic acid preparation method and belongs to the field of radioisotope C labeled compounds. C-labeled α - naphthylacetic acid preparation method, C radioisotope labeling is introduced on a naphthalene ring structure α -naphthol acid, C labeling site is in α-position. The method has the advantages that the reaction raw materials are easily available, the synthesis steps are high in yield, the total yield is more 60%, C marker isotopes are less in use amount, and waste is generated. The marker site α-position on the naphthalene ring is less likely to be metabolized compared to C-labeled branched acetic acid, and the synthesized C-labeled compound provides a better study of α -naphthoic acid in the environment.
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- Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
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α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.
- Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 7082 - 7086
(2021/02/26)
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- One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
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We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
- Bobal, Pavel,Otevrel, Jan,Svestka, David
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p. 25029 - 25045
(2020/07/14)
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- Synthesis, Antiviral, Antibacterial, and Cytotoxicity Assessment of Some 3H-Benzo[a]imidazo[4,5-j]acridines and 3H-Benzo[a]pyrazolo[3,4-j]acridines
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Abstract: Some novel 3H-benzo[a]imidazo[4,5-j]acridines and 3H-benzo[a]pyrazolo[3,4-j]acridines were synthesized by the reaction of 1-alkyl-5-nitro-1H-benzoimidazoles and 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile in high yields. The structures of the new compounds were determined by spectral (FTIR, 1H, and 13C NMR) and analytical data. The antiviral activity of the synthesized compounds was tested against a panel of DNA and RNA viruses, including herpes simplex virus-1 KOS, vesicular stomatitis virus, herpes simplex virus-2 (G), vaccinia virus, and herpes simplex virus-1 TK-KOS ACVr. Most of the test compounds showed moderate activities in comparison with their corresponding reference standards. The synthesized compounds were also tested for antibacterial activity against a panel of strains of gram-negative and gram-positive bacterial species, and some of them we found as effective against gram- positive bacteria as well-known antibacterial agents, such as Cephalexin. The products we found to be cytostatic in the higher micromolar range.
- Faramarzi, M.,Morsali, A.,Pordel, M.
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p. 1438 - 1445
(2020/10/02)
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- HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles
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We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is
- Hammond, Gerald B.,Mudshinge, Sagar R.,Potnis, Chinmay S.,Xu, Bo
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supporting information
p. 4161 - 4164
(2020/07/14)
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- Naphthylacetic acid preparation method
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The invention discloses a naphthylacetic acid preparation method, which comprises: naphthylacetic acid is prepared by using 1-chloromethylnaphthalene as a starting raw material, using cuprous iodide as a catalyst, using potassium ferrocyanide as a cyanide source and adding triethyl benzyl ammonium chloride as a phase transfer catalyst into a reaction system. According to the invention, traditionalpotassium cyanide or sodium cyanide is replaced with potassium ferrocyanide as the cyanide source, so the safety threat of potassium cyanide or sodium cyanide to operators in a production process isavoided, and environment pollution caused by highly toxic substances is reduced; and the preparation method has advantages of simple post-treatment, low energy consumption and few three-waste.
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Paragraph 0037; 0039; 0040; 0047; 0049; 0050; 0057; 0059
(2020/03/12)
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- Benzylamine derivatives and its application on the medicament
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The invention provides novel benzylamine derivatives or stereoisomers, geometric isomers, tautomers, nitric oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salt or prodrugs of the benzylamine derivatives, which are used for treatin
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- Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters
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A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.
- Michel, Nicholas W. M.,Jeanneret, Alexandria D. M.,Kim, Hyehwang,Rousseaux, Sophie A. L.
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p. 11860 - 11872
(2018/10/02)
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- Synthesis, Spectral Studies, and Quantum Chemical Investigations of a New Violet Dye and a Fluorescent Heterocyclic System
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The new violet dye 3-(hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-2-(naphthalen-1-yl) acetonitrile was synthesized by reaction of 3-nitro-imidazo[1,2-a]pyridine with 1-naphthylacetonitrile. Cyclization of the latter compound in pyridine led to the formation of new fluorescent heterocyclic system benzo[f]pyrido[2’,1’:2,3] imidazo[4,5-b]quinoline. The structural assignments of the new compounds were based on their spectral and microanalytical data. The optical and solvatochromic properties of the compounds were investigated, and the results showed that they display interesting photophysical properties such as high values of extinction coefficient and fluorescence quantum yield. Moreover, the density functional theory (DFT) calculations were employed to gain a deeper insight into the geometry and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained by the time-dependent DFT method.
- Alipoor, Hamideh,Pordel, Mehdi,Morsali, Ali
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p. 313 - 319
(2018/09/26)
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- 3H-Benzo[a]imidazo[4,5-j]acridine as a new fluorescent heterocyclic system: synthesis, spectral studies, and quantum chemical investigation
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The synthesis, spectral studies, and theoretical calculations of a new fluorescent heterocyclic system are described. New 3H-benzo[a]imidazo[4,5-j]acridines were obtained in high yields by the reaction of 1-alkyl-5-nitro-1H-benzimidazoles with (naphthalen-1-yl)acetonitrile via nucleophilic substitution of hydrogen, and their structures were established by spectral (UV-Vis, FT-IR, 1H and 13C NMR) and analytical data. Study of the optical and solvatochromic properties of the dyes revealed their high molar absorption coefficients and high fluorescence quantum yields which in some cases exceeded quantum yields of well-known fluorescent dyes such as fluorescein. Density functional theory (DFT) calculations using the B3LYP hybrid functional and 6-311++G(d,p) basis set were performed to obtain optimized geometries and frontier orbital structures of the synthesized compounds. The electronic absorption spectra were also simulated by the time-dependent density functional theory (TD-DFT) method.
- Alipoor,Pordel,Morsali
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p. 1586 - 1592
(2017/12/07)
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- Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
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A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
- Das, Riki,Kapur, Manmohan
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p. 1114 - 1126
(2018/06/18)
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- Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted SNAr Reaction
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Fluoroarenes bearing no electron-withdrawing groups (non-activated fluoroarenes) readily underwent nucleophilic aromatic substitution with α-cyanocarbanions under microwave irradiation. The sequence (i) formylalkylation involving the cyanoalkylation of fl
- Fuchibe, Kohei,Imaoka, Hisanori,Ichikawa, Junji
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supporting information
p. 2359 - 2363
(2017/09/06)
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- One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions
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A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.
- Ezawa, Masatoshi,Togo, Hideo
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p. 2379 - 2384
(2017/05/01)
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- SULFONAMIDE DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF
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Provided herein are sulfonamide derivatives or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, and their uses for treating Alzheimer's disease. Also provided herein are pharmaceutical compositions containing such compounds, and use of such compounds or pharmaceutical compositions thereof for managing or treating 5-HT6 receptor-mediated diseases, especially in the manufacture of a medicament for managing or treating Alzheimer's disease.
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- The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes
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The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)
- Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.
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supporting information
p. 50 - 53
(2015/07/28)
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- Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids
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Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.
- Wu, Guojiao,Deng, Yifan,Wu, Chaoqiang,Zhang, Yan,Wang, Jianbo
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supporting information
p. 10510 - 10514
(2016/02/18)
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- Pd-catalyzed cyanation of benzyl chlorides with nontoxic K 4[Fe(CN)6]
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Non-toxic K4[Fe(CN)6] was demonstrated to be effective as a green cyanating agent for the cyanation of alkyl halides using PPh3/Pd(OAc)2 as a catalyst system. The presented method allowed a series of benzyl chlorides to be smoothly cyanated in up to 88% yield. In order to avoid or suppress the deactivation of the catalyst, the reaction was required to be performed in a stringent inert ambiance.
- Ren, Yunlai,Yan, Mengjie,Zhao, Shuang,Sun, Yanpei,Wang, Jianji,Yin, Weiping,Liu, Zhifei
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scheme or table
p. 5107 - 5109
(2011/10/05)
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- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
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Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
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- Facile synthesis of nitriles from primary nitro compounds via nitrolic acids and their esters
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The reactions of alkane- and arylalkanenitrolic acids esters Bu3SnH in the presence of a catalytic amount of AIBN in refluxing benzene afforded the corresponding nitriles in excellent yields.
- Chang, Rae Kyu,Kim, Kyongtae
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p. 7791 - 7794
(2007/10/03)
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- Degradation of 3-aryl-2-hydroxyiminopropionic acids into arylacetonitriles using 1,1'-carbonyldiimidazole or 2,2'-oxalyldi(o-sulfobenzimide)
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1,1'-Carbonyldiimidazole (1) is a useful reagent for the preparation of arylacetonitriles (9) from 3-aryl-2-hydroxyiminopropionic acids (8), and 2,2'-oxalyldi (o-sulfobenzimide) (2) can also be used for this purpose under essentially neutral conditions.
- Kitagawa,Kawaguchi,Inoue,Katayama
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p. 3030 - 3033
(2007/10/02)
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- EFFECTS OF SUBSTITUENTS IN THE EQUILIBRIUM CH AND NH ACIDITY OF SUBSTITUTED 1-NAPHTHYLACETONITRILES AND 1-NAPHTHYLAMINES
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The pK values of the CH and NH acids of 4-substituted 1-naphthylacetonitriles 1,4-RC10H6CH2CN and 1-naphthylamines 1,4-RC10H6NH2 (R = CH3, H, Cl, Br, CN, NO2) were determined by the transmetallation method in dimethyl sulfoxide (with the K+ cat
- Terekhova, M.I.,Os'kina, I.A.,Sutula, V.D.,Rogozhnikova, O.Yu.,Tabatskaya, A.A.,et al.
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p. 361 - 369
(2007/10/02)
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- A Facile Synthesis of Nitriles from 1-Nitro-1-alkenes by Electroreduction
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Electroreduction of 1-nitro-1-alkenes in the presence of titanium(IV) chloride affords nitriles in good yields.This procedure provides a facile transformation of aldehydes to one-carbon elongated nitriles since the 1-nitro-1-alkenes are best prepared from aldehydes and nitromethane.
- Sera, Akira,Tani, Hiroyuki,Nishiguchi, Ikuzo,Hirashima, Tsuneaki
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p. 631 - 633
(2007/10/02)
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- FACILE CONVERSION OF CARBOXAMIDES TO NITRILES
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Alkyl, aralkyl, aryl, heteroaryl carboxamides bearing various functionalities are readily converted to the corresponding nitriles in good yields using the liquid "diphosgene", trichloromethyl chloroformate, as dehydrating agent.In many cases, the procedure does not require extraction, and hence offers a very simple work-up.
- Mai, Khuong,Patil, Ghanshyam
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p. 2203 - 2206
(2007/10/02)
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- A Comparative Study of Photoinduced Isomerizations between 1-exo- and 1-endo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalenes
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The titled compounds 1-exo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalenes(8a), 1-endo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalenes(8b), were photolyzed in several solvents.The results were: (1) The isomerization proceeded faster in aprotic nonpolar
- Kobayashi, Hisako,Kato, Masahiko,Miwa, Toshio
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p. 490 - 496
(2007/10/02)
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- Reaction of Aryl Aldehydes with Thiocyanates in the Presence of Tributylphosphine
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Aryl aldehydes react with methyl thiocyanate in the presence of tributylphosphine to afford S-methyl thiobenzoates and arylacetonitriles in good yields.This is a novel disproportionation reaction involving carbon-carbon bond formation.These compounds thus obtained are easily converted into deoxybenzoins using sodium hydride.On the other hand, p-dialkylaminobenzaldehydes react with methyl thiocyanate under the same conditions to furnish both the corresponding trans-dicyanostilbenes and succinonitriles in moderate yields.Finally, the reaction was carried out with aryl thiocyanates resulting in the formation of addition products.
- Yokoyama, Masataka,Ohteki, Hiroko,Kurauchi, Masahiko,Hoshi, Kazuko,Yanagisawa, Eizaburo,et al.
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p. 2635 - 2640
(2007/10/02)
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- Conformational Effects in Fluorescent Excited Charge-transfer Complex Formation
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From a study if the variation in fluorescence quantum yield and lifetime with change in solvent polarity for some ω-(1-naphthyl)-N-alkylpyrroles it is concluded that the conformation of the excited complex has little effect upon the wavelength of fluorescence but does have an effect upon the relative efficiencies of the radiative and non-radiative decay processes.
- Luo, Xiu-Jin,Beddard, Godfrey S.,Porter, George,Davidson, R. Stephen,Whelan, Terence D.
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p. 3467 - 3476
(2007/10/02)
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- Syntheses of Arylacetone and Arylacetonitrile by Friedel-Crafts Reaction with α-Chloro-α-(methylthio)-substituted Acetone and Acetonitrile
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Novel preparative methods for arylacetone and arylacetonitrile are described.Friedel-Crafts reactions of aromatic compounds with α-chloro-α-(methylthio)acetone (4) and α-chloro-α-(methylthio)acetonitrile (7) in the presence of Lewis acid afforded α-(methylthio)arylacetone (5) and α-(methylthio)arylacetonitrile (8), respectively.Compounds (5) and (8) were converted into the corresponding arylacetone (6) and arylacetonitrile (9) by reduction with zinc dust in acetic acid.Keywords: Friedel-Crafts reaction with α-chloro-α-(methylthio)acetone; Friedel-Crafts reaction with α-chloro-α-(methylthio)acetonitrile; α-(methylthio)arylacetone; α-(methylthio)arylacetonitrile; arylacetone; arylacetonitrile; reductive desulfurization; zinc dust-acetic acid
- Tamura, Yasumitsu,Choi, Hong Dae,Mizutani, Masako,Ueda, Yuko,Ishibashi, Hiroyuki
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p. 3574 - 3579
(2007/10/02)
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- Photochemical Aromatic Cyanomethylation
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Cyanomethylation is accomplished by the photolysis of chloroacetonitrile in the presence of aromatics by way of electron transfer followed by radical coupling.
- Lapin, Stephen,Kurz, Michael E.
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p. 817 - 818
(2007/10/02)
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- A NOVEL DISPROPORTIONATION REACTION OF AROMATIC ALDEHYDES INVOLVING C-C BOND FORMATION
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The reaction of aromatic aldehydes with methyl thiocyanate in the presence of tributylphosphine afforded both S-methyl thiobenzoates and phenylacetonitriles via a novel disproportionation pathway involving carbon-carbon bond formation.
- Kurauchi, Masahiko,Imamoto, Tsuneo,Yokoyama, Masataka
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p. 4985 - 4986
(2007/10/02)
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