- A new, efficient, and simple method for the synthesis of thiiranes from epoxides under solvent-free conditions
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A simple, efficient, and new method has been developed for the synthesis of thiiranes from epoxides through a one-pot reaction of epoxides with diethyl phosphite in the presence of ammonium acetate or ammonium hydrogen carbonate/sulfur/ and acidic alumina under solvent-free conditions using microwave irradiation.
- Kaboudin, Babak,Norouzi, Hamid
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- LASER INDUCED SYNTHESYS: SELECTIVE FORMATION OF CYCLOHEXENE EPISULPHIDE FROM MOLECULAR SULPHUR S8
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1,2-Epithiocyclohexane was obtained selectively by irradiation of a mixture of cyclohexene and sulphur with a pulsed laser (266 nm).
- Bertaina, C.,Fellous, R.,Lemaire, F.,Stringat, R.
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- Preparation, characterization and application of MgFe2O4/Cu nanocomposite as a new magnetic catalyst for one-pot regioselective synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles
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Magnesium ferrite magnetic nanoparticles were synthesized by a solid-state reaction of magnesium nitrate, hydrated iron(iii) nitrate, NaOH and NaCl salts and then calcined at high temperatures. In order to prevent oxidation and aggregation of magnesium ferrite particles, and also for preparing a new catalyst of supported copper on the magnetic surface, the MgFe2O4was covered by copper nanoparticles in alkaline medium. Magnetic nanoparticles of MgFe2O4/Cu were successfully obtained. The structure of the synthesized magnetic nanoparticles was identified using XRD, TEM, EDS, FT-IR, FESEM and VSM techniques. The prepared catalyst was used in the three component one-pot regioselective synthesis of 1,2,3-triazoles in water. The various thiiranes bearing alkyl, allyl and aryl groups with terminal alkynes, and sodium azide in the presence of the MgFe2O4/Cu nanocatalyst were converted to the corresponding β-thiolo/benzyl-1,2,3-triazoles as new triazole derivatives. The effects of different factors such as time, temperature, solvent, and catalyst amount were investigated, and performing the reaction using 0.02 g of catalyst in water at 60 °C was chosen as the optimum conditions. The recovered catalyst was used several times without any significant change in catalytic activity or magnetic property.
- Eisavi, Ronak,Naseri, Kazhal
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p. 13061 - 13076
(2021/04/22)
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- Precise Synthesis of Poly(thioester)s with Diverse Structures by Copolymerization of Cyclic Thioanhydrides and Episulfides Mediated by Organic Ammonium Salts
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The precise synthesis of poly(thioester)s with diverse structures is still a significant challenge in the polymeric materials field. Herein, we report a novel approach to the synthesis of well-defined poly(thioester)s by the controlled alternating copolymerization of cyclic thioanhydrides and episulfides induced by simple organic ammonium salts. Both the cation and anion have strong effects on the copolymerization. [PPN]OAc ([PPN]=bis(triphenylphosphine)iminium) with a bulky cation was proven to be efficient in initiating this polymerization, yielding poly(thioester)s with a completely alternating structure, controlled molecular weight, and narrow polydispersity. The poly(thioester) obtained from succinic thioanhydride and propylene sulfide is a typical semicrystalline material, possessing a high refractive index of up to 1.78. Because it uses readily available monomers, this method is expected to open up a new route to poly(thioester)s with diverse structures and properties.
- Yue, Tian-Jun,Zhang, Ming-Chao,Gu, Ge-Ge,Wang, Li-Yang,Ren, Wei-Min,Lu, Xiao-Bing
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supporting information
p. 618 - 623
(2019/01/04)
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- Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe2O4/Mg(OH)2 nanocomposite in water under benign conditions
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The magnetically separable CuFe2O4/Mg(OH)2 nanocomposite was prepared and characterized by FT-IR, XRD, SEM, EDS, and VSM techniques. The synthesized nanoparticles were used as a new and efficient heterogeneous catalyst for the conversion of various epoxides to the corresponding thiiranes with thiourea in water solvent at room temperature. The reactions were completed within 1–3.7 h to give thiiranes in 70–99% yields. The applied CuFe2O4/Mg(OH)2 nanocomposite was separated easily using an external magnet and reused for several times without any considerable loss of activity.
- Hassanzadeh, Shadi,Eisavi, Ronak,Abbasian, Mojtaba
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p. 240 - 255
(2019/01/30)
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- Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
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A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
- Dong, Jun,Xu, Jiaxi
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p. 2407 - 2415
(2018/04/16)
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- A green method for solvent-free conversion of epoxides to thiiranes using NH4SCN in the presence of NiFe2O4 and MgFe2O4 magnetic nanocatalysts
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Nickel and magnesium ferrite magnetic nanoparticles were fabricated and applied as efficient and reusable catalysts in the solvent-free conversion of various epoxides to the corresponding thiiranes with ammonium thiocyanate under oil bath (60°C) conditions. NiFe2O4 and MgFe2O4 nanoparticles can catalyze the reactions at short times in high to excellent yields. The catalysts can also be recovered easily using an external magnetic field and be reused four times without any significant loss of activity.
- Eisavi, Ronak,Ahmadi, Fatemeh,Ebadzade, Behrooz,Ghadernejad, Seiran
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p. 614 - 624
(2017/10/03)
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- Synthesis of 3-acyl-5,6-dihydro-1,4-oxathiines through ring expansion of thiiranes
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Synthesis of 3-acyl-5,6-dihydro-1,4-oxathiines has been achieved via reactions of thiiranes and α-diazo-β-1,3-dicarbonyl compounds under microwave and copper sulfate-assisted conditions. The current method provides a direct and simple strategy in efficient preparation of 3-acyl-1,4-oxathiines from readily available thiiranes and trans-3-acyl-5,6-dihydro-1,4-oxathiines as stereospecific products for 1,2-disubstituted cis-thiiranes. The reaction mechanism was also proposed.
- Chen, Xingpeng,Xu, Jiaxi
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supporting information
p. 1651 - 1654
(2017/04/04)
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- Tuning diastereoisomerism in platinum(ii) phosphino- and aminothiolato hydrido complexes
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Chelate assisted oxidative addition of one equivalent of 2-phosphinothiols (2-(diphenylphosphino)ethanethiol 1, 1-(benzyloxy)-2-(diphenylphosphino)ethanethiol 2 and 2-(diphenylphosphino)-cyclohexanethiol 3) to tetrakis(triphenylphosphine)platinum(0) gives the corresponding hydrido[2-(phosphino-κP)thiolato-κS]triphenylphosphineplatinum(ii) complexes 8-10. Temperature variable NMR studies show that these complexes display a chemical equilibrium between the cis-P,P and trans-P,P geometries, strongly displaced toward the trans-P,P configuration (70-90%). XRD studies carried out on crystals of 8 indicate that although the two geometric isomers are present in solution, only the trans-P,P is obtained in the solid state. These results differ from the cis-P,N geometry observed for the related hydrido[2-(amino-κN)thiolato-κS]triphenylphosphineplatinum(ii) complexes 5-7 in solution. The crystal structures obtained for these aminothiolate hydrides show that the cis-P,N configuration is the only one observed in the solid state. Chelate assisted oxidative addition of one equivalent of 3-(diphenylphosphino)propanethiol 4 to tetrakis(triphenylphosphine)platinum(0) gives the resultant hydrido[3-(phosphino-κP)thiolato-κS]triphenylphosphineplatinum(ii) complex 11. This 3-phosphinothiolate hydride shows in solution only a trans-P,P geometry but presents two chelate ring conformational isomers. Density functional theory calculations have been used to explore the ligand-based stereoelectronic effects that are determinant in the different diastereoisomerism observed in these platinum(ii) hydrides (5-11).
- Polo,Duran,Juanola,Real,Benet-Buchholz,Solà,Poater
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p. 3015 - 3028
(2017/04/14)
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- A green protocol for rapid and efficient conversion of epoxides to thiiranes using alumina immobilized thiourea at solvent-free conditions
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Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out successfully with alumina-immobilized thiourea at room temperature. The reactions were completed within 2-9 min to give thiiranes with 83-98% yields. The utilized alumina can be reused for several times without losing its activity.
- Eisavi, Ronak,Zeynizadeh, Behzad
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- Magnetically separable nano CuFe2O4: an ef?cient and reusable heterogeneous catalyst for the green synthesis of thiiranes from epoxides with thiourea
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The magnetically separable nano CuFe2O4 was prepared and used as an efficient heterogeneous catalyst for conversion of various epoxides to the corresponding thiiranes with thiourea in refluxing ethanol. The reactions were completed within 34?45 min to give thiiranes in 80?95% yields. The utilized nano CuFe2O4 can be reused for several times without losing its activity.
- Eisavi, Ronak,Ghadernejad, Seiran,Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh
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p. 537 - 545
(2016/10/03)
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- Atom economical synthesis of di- and trithiocarbonates by the lithium: Tert -butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes
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Alkali metal alkoxides were studied as catalysts for the addition of CS2 to epoxides. A screening of several commercially available alkoxides revealed lithium tert-butoxide as an active and selective catalyst for this reaction. The influence of different reaction parameters as well as the substrate scope under optimized reaction conditions has been studied. Terminal and highly substituted epoxides as well as thiiranes were converted. In total 28 products were prepared and isolated in yields up to 95%. Notably, the reactions were performed under mild conditions without additional solvents. The regio- and stereoselectivity of the reaction has been studied e.g. by converting (R)-styrene and (R)-propylene oxide. Moreover, the test reaction was monitored by 13C NMR and a plausible mechanism for the conversion of terminal and internal epoxides is given. This proposal is in agreement with the observed regio- and stereoselectivity of the reaction.
- Diebler,Spannenberg,Werner
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supporting information
p. 7480 - 7489
(2016/08/16)
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- An efficient and improved method for the conversion of oxiranes into thiiranes using graphite oxide
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An efficient and improved procedure has been developed for the conversion of oxiranes into thiiranes using sodium thiocyanate in the presence of graphite oxide under solvent-free conditions at an ambient temperature in excellent yields and in short reaction times.
- Mirza-Aghayan, Maryam,Molaee Tavana, Mahdieh
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- Odourless strategy for deep eutectic solvent-mediated ring opening of epoxides with in situ generated S -alkylisothiouronium salts
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A general, straightforward and odourless ring-opening reaction allows the preparation of β-hydroxy sulfides from in situ generated S-alkylisothiouronium salts in urea-choline chloride-based deep eutectic solvent (DES). In addition, reaction of epoxides with thiourea in DES yields the corresponding thiiranes. Georg Thieme Verlag Stuttgart New York.
- Azizi, Najmedin,Yadollahy, Zahra,Rahimzadeh-Oskooee, Amin
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p. 1085 - 1088
(2014/05/20)
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- A facile and convenient method for synthesis of thiiranes under mild condition using phase transfer catalyst
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A mild and efficient process for preparation of thiiranes with KSCN in water at room temperature using a catalytic amount of 1,4- bis(triphenylphosphonium)-2-butene dichloride is described.
- Gorjizadeh, Maryam,Afshari, Mozhgan
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p. 1657 - 1660
(2014/05/06)
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- Green synthesis of thiiranes from oxiranes under solvent- and catalyst-free conditions
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A simple and efficient method for the conversion of oxiranes to thiiranes using ammonium thiocyanate (NH4SCN) under solvent- and catalyst-free conditions is described. These conditions enable clean and fast conversion of oxiranes to the corresponding thiirane.
- Akhlaghinia, Batool,Rahimizadeh, Mohammad,Eshghi, Hosein,Zhaleh, Sara,Rezazadeh, Soodabeh
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experimental part
p. 351 - 361
(2012/08/27)
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- Zeolite molecular sieve 4: A reusable catalyst for fast and efficient conversion of epoxides to thiiranes with thiourea
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Various epoxides are readily converted to their corresponding thiiranes by thiourea/zeolite molecular sieve 4 system in refluxing MeOH. All reactions were carried out within 12-25 min to give thiiranes in 80%-99% yields. The catalyst saves its catalytic activity for several times at this transformation. Stereospecific conversion of (R)-(+)-styrene oxide to (S)-(+)-styrene episulfide was achieved by this combination system. Taylor & Francis Group, LLC.
- Eisavi, Ronak,Zeynizadeh, Behzad,Baradarani, Mohammad Mehdi
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experimental part
p. 1902 - 1909
(2011/10/09)
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- A practical and eco-friendly method for conversion of epoxides to thiiranes with immobilized thiourea on CaCO3
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Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out efficiently with immobilized thiourea on CaCO3. The reactions were completed within 1-12 min under oil bath (60 °C-70 °C) conditions to afford thiiranes in 88%-98% yields. Copyright Taylor & Francis Group, LLC.
- Zeynizadeh, Behzad,Baradarani, Mohammad Mehdi,Eisavi, Ronak
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experimental part
p. 2208 - 2215
(2012/04/04)
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- Reaction of optically active oxiranes with thiofenchone and 1-methylpyrrolidine-2-thione: Formation of 1,3-oxathiolanes and thiiranes
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The SnCl4-catalyzed reaction of (-)-thiofenchone (=1,3,3-trimethylbicyclo[2.2.1]heptane-2-thione; 10) with (R)-2-phenyloxirane ((R)-11) in anhydrous CH2Cl2 at -60° led to two spirocyclic, stereoisomeric 4-phenyl-1,3-oxathiolanes 12 and 13 via a regioselective ring enlargement, in accordance with previously reported reactions of oxiranes with thioketones (Scheme 3). The structure and configuration of the major isomer 12 were determined by X-ray crystallography. On the other hand, the reaction of 1-methylpyrrolidine-2-thione (14a) with (R)-11 yielded stereoselectively (S)-2-phenylthiirane ((S)-15) in 56% yield and 87-93% ee, together with 1-methylpyrrolidin-2-one (14b). This transformation occurs via an SN2-type attack of the S-atom at C(2) of the aryl-substituted oxirane and, therefore, with inversion of the configuration (Scheme 4). The analogous reaction of 14a with (R)-2-{[(triphenylmethyl)oxy] methyl}oxirane ((R)-16b) led to the corresponding (R)-configured thiirane (R)-17b (Scheme 5); its structure and configuration were also determined by X-ray crystallography. A mechanism via initial ring opening by attack at C(3) of the alkyl-substituted oxirane, with retention of the configuration, and subsequent decomposition of the formed 1,3-oxathiolane with inversion of the configuration is proposed (Scheme 5). Copyright
- Fu, Changchun,Linden, Anthony,Heimgartner, Heinz
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experimental part
p. 773 - 784
(2011/06/27)
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- Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides
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In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.
- Taghavi, S. Abdolmanaf,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Ahmadi, Venus
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experimental part
p. 2244 - 2252
(2011/10/03)
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- Silica chloride-catalyzed synthesis of thiiranes from oxiranes under solvent-free conditions
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A mild, simple, and efficient method for the synthesis of thiiranes from epoxides using a catalytic amount of silica chloride under solvent-free conditions has been developed. Experimental simplicity, simple work-up procedure, and solvent-free reaction conditions are important features of the present protocol. Copyright Taylor & Francis Group, LLC.
- Wu, Liqiang,Yang, Limin,Fang, Lizhen,Yang, Chunguang,Yan, Fulin
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experimental part
p. 2159 - 2164
(2010/11/19)
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- A green protocol for solvent-free conversion of epoxides to thiiranes with Dowex-50WX8-supported thiourea
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Structurally different epoxides were efficiently converted to the corresponding thiiranes by Dowex-50WX8-supported thiourea under solvent-free conditions. The reactions were carried out either in an oil bath or under microwave irradiation to give the thiiranes in 75-98% yields within 30 sec-120 min.
- Zeynizadeh, Behzad,Yeghaneh, Samal
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experimental part
p. 362 - 368
(2009/09/25)
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- Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature
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Herein we shed light on the mechanism of the reaction of epoxides with ammonium thiocyanate to give the corresponding thiiranes in water, and we present a computational mechanistic model for this highly useful reaction.
- Kleiner, Christian M.,Horst, Luise,Wuertele, Christian,Wende, Raffael,Schreiner, Peter R.
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supporting information; experimental part
p. 1397 - 1403
(2009/12/04)
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- LiClO4 catalyzed mild and efficient method for the synthesis of thiiranes from oxiranes
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Oxiranes are efficiently converted to the corresponding thiiranes by potassium thiocyanate in the presence of catalytic amounts of LiClO4 with excellent yields under mild and nonaqueous conditions.
- Reddy, Ch. Sanjeeva,Nagavani
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- Solvent-free conversion of epoxides to thiiranes by thiourea/NH4Cl system
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Epoxides were readily converted to the corresponding thiiranes by thiourea/NH4Cl system under solvent-free conditions. The reactions were completed within 15-75 min at 60-70°C. The thiiranes were obtained in 65-96% yields. Copyright Taylor & Francis Group, LLC.
- Zeynizadeh, Behzad,Yeghaneh, Samal
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experimental part
p. 2280 - 2286
(2009/08/07)
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- 2,4,6-Trichloro-1,3,5-triazine catalyzed synthesis of thiiranes from oxiranes under solvent-free and mild conditions
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A simple, mild and efficient method has been developed for the synthesis of thiiranes from epoxides using a catalytic amount of 2,4,6-trichloro-1,3,5-triazine under solvent-free conditions.
- Bandgar,Joshi, Neeta S.,Kamble
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p. 4775 - 4777
(2007/10/03)
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- Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)
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Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.
- Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Yadollahi, Bahram,Mirmohammadi, S. Mohammad R.
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p. 235 - 242
(2007/10/03)
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- An efficient catalyst-free synthesis of thiiranes from oxiranes using polyethylene glycol as the reaction medium
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A catalyst-free, high-yielding conversion of oxiranes into thiiranes has efficiently been carried out by treatment with KSCN or thiourea at room temperature using polyethylene glycol (PEG-400) as the reaction medium.
- Das, Biswanath,Reddy, V. Saidi,Krishnaiah
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p. 8471 - 8473
(2007/10/03)
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- A green protocol for the easy synthesis of thiiranes from epoxides using thiourea/silica gel in the absence of solvent
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The use of thiourea/silica gel provides a green protocol for the easy and high-yielding preparation of thiiranes from different classes of epoxides in the absence of solvent at room temperature. The high stereospecific conversion of (R)(+)-styrene oxide to (S)(+)-styrene sulfide is also reported using this reagent system. Copyright Taylor & Francis Inc.
- Iranpoor, Nasser,Firouzabadi, Habib,Jafari, Abbas Ali
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p. 1809 - 1814
(2007/10/03)
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- Conversion of oxiranes to thiiranes catalyzed with silica gel-supported aluminium chloride
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Silica gel-supported aluminium chloride, SiO2-AlCl3, catalysizes the efficient conversion of different oxiranes to their corresponding thiiranes in the presence of thiourea under nonaqueous conditions. Copyright Taylor & Francis, Inc.
- Borujeni, K. Parvanak
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p. 2575 - 2579
(2007/10/03)
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- Ring enlargement and sulfur-transfer processes in SiO2-catalyzed reactions of thiocarbonyl compounds with optically active oxiranes
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The reactions of 1,3-dioxolane-2-thione (3) with (S)-2-methyloxirane ((S)-1) and with (R)-2-phenyloxirane ((R)-2) in the presence of SiO2 in anhydrous dichloroalkanes led to the optically active spirocyclic 1,3-oxathiolanes 8 with Me at C(7) and 9 with Ph at C(8), respectively (Schemes 2 and 3). The analogous reaction of 1,3-dimethylimidazolidine-2-thione (4a) with (R)-2 yielded stereoselectively (S)-2-phenylthiirane ((S)-10) in 83% yield and 97% ee together with 1,3-dimethylimidazolidin-2-one (11a). In the cases of 3-phenyloxazolidine-2-thione (4b) and 3-phenylthiazolidine-2-thione (4c), the reaction with (RS)-2 yielded the racemic thiirane (RS)-10, and the corresponding carbonyl compounds 11b and 11c (Scheme 4 and Table 1). The analogous reaction of 4a with 1,2-epoxycyclohexane (=7-oxabicyclo[4.1.0]heptane; 7) afforded thiirane 12 and the corresponding carbonyl compound 11a (Scheme 5). On the other hand, the BF3-catalyzed reaction of imidazolidine-2-thione (5) with (RS)-2 yielded the imidazolidine-2-thione derivative 13 almost quantitatively (Scheme 6). In a refluxing xylene solution, 1,3-diacetylimidazolidine-2-thione (6) and (RS)-2 reacted to give two imidazolidine-2-thione derivatives, 13 and 14 (Scheme 7). The structures of 13 and 14 were established by X-ray crystallography (Fig.).
- Malaschichin, Sergej,Fu, Changchun,Linden, Anthony,Heimgartner, Heinz
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p. 3253 - 3262
(2007/10/03)
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- Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin
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The new electron deficient tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(tpp)(OTf)2], was used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides. Conversion of epoxides to thiiranes and acetonides were also performed efficiently in the presence of this catalyst.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Shaibani, Reza
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p. 6105 - 6111
(2007/10/03)
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- Synthesis of thiiranes from oxiranes in water using polymeric cosolvents
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Poly(vinylamine) (PVA) and poly(allylamine) (PAA) were prepared and used as polymeric cosolvents. Oxiranes were converted efficiently to the corresponding thiiranes under mild reaction conditions in water with ammonium thiocyanate (NH4SCN) using these polymeric cosolvents. The polymeric cosolvents are reusable.
- Tamami, Bahman,Kolahdoozan, Majid
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p. 1535 - 1537
(2007/10/03)
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- Titanium dioxide as a mild and efficient catalyst for conversion of epoxides to thiiranes
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Titanium dioxide (TiO2) efficiently catalyze the reaction of a variety of epoxides with ammonium thiocyanate in refluxing acetonitrile to afford the corresponding thiirane in high to excellent yields.
- Yadollahi, Bahram,Tangestaninejad, Shahram,Habibi, Mohammad Hossein
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p. 2823 - 2827
(2007/10/03)
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- Synthesis of Thiiranes from Oxiranes Using Cross-Linked Polystyrene Supported Aluminium Chloride as a Catalyst
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A simple and efficient method for conversion of oxiranes to their corresponding thiiranes using thiourea catalyzed with cross-linked polystyrene supported aluminium chloride, (Ps-AlCl3), under non-aqueous condition is described.
- Tamami,Borujeny, K. Parvanak
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- Synthesis of thiiranes from oxiranes in the presence of β-cyclodextrin in water
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A mild and highly efficient, user-friendly procedure has been developed for the conversion of oxiranes to thiiranes under supramolecular catalysis in the presence of β-cyclodextrin in water at ambient temperature in excellent yields. The use of β-cyclodextrin in this transformation overcomes the use of heavy metal halides as promoters and chlorinated hydrocarbons and other hazardous organic solvents.
- Srilakshmi Krishnaveni,Surendra,Somi Reddy,Nageswar,Rama Rao
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p. 395 - 397
(2007/10/03)
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- A new and efficient method for the synthesis of thiiranes from oxirane-β-cyclodextrin complexes and thiourea in water
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Oxiranes react smoothly with thiourea in the presence of β-cyclodextrin in water at room temperature under neutral conditions to afford the corresponding thiiranes in excellent yields; the β-cyclodextrin can be recycled.
- Surendra,Krishnaveni, N. Srilakshmi,Rao, K. Rama
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p. 6523 - 6526
(2007/10/03)
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- A convenient synthesis of phosphorodithioates and novel conversion of epoxides to thiiranes
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Alumina-supported ammonium acetate under microwave irradiation was found to be an efficient reagent for the preparation of phosphorodithioates from phosphorus pentasulfide under solvent-free condition. A simple, efficient, and new method has been developed for the synthesis of thiiranes from epoxides through a one-pot reaction of epoxides with the mixture of phosphorus pentasulfide in the presence of ammonium acetate and acidic alumina under reflux in EtOH or solvent-free conditions under microwave irradiation. These methods are easy, rapid, and good-yielding reactions for the synthesis of phosphorodithioates and thiiranes.
- Kaboudin, Babak,Norouzi, Hamid
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p. 2035 - 2039
(2007/10/03)
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- Solvent-free conversion of oxiranes to thiiranes with thiourea
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A simple and efficient method for the conversion of various oxiranes to the corresponding thiiranes using thiourea under solvent free conditions is described.
- Kiasat, Ali Reza,Kazemi, Foad,Jardi, Mehdi Fallah Mehr
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p. 1841 - 1844
(2007/10/03)
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- Conversion of epoxides into 2-hydroxyethyl thiocyanates with NH 4SCN in the presense of 2,6-BIS[2-(O-amino phenoxy)methyl]-4-bromo-1- methoxybenzene (BABMB) as catalyst
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A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) is described. In this study, a reagent and conditions have been discovered with which the individual 2-hydroxyethyl thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.
- Niknam, Khodabakhsh
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p. 499 - 506
(2007/10/03)
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- [Bmim]PF6: A novel and recyclable ionic liquid for conversion of oxiranes to thiiranes in aqueous media
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A variety of epoxides respond rapidly with potassium thiocyanate in [bmim]PF6-H2O (2:1) solvent system at room temperature under mild and convenient conditions to produce the corresponding thiiranes in high to quantitative yields. Enhanced rates, improved yields, and recyclability of ionic liquids are the remarkable features observed in ionic liquids (ILs). The use of ionic liquids for this transformation avoids the use of heavy metal halides as promoters and chlorinated hydrocarbons as solvents. The ionic liquid was recycled in five to six subsequent runs with gradual decrease in activity.
- Yadav,Reddy,Srinivas, Ch.,Rajasekhar, Reddy K.
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p. 2525 - 2527
(2007/10/03)
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- Magnesium hydrogensulfate: A cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO4)2, with high degree of regioselectivity. The reactions are chemoselective and many of the other functional groups such as ethereal carbon oxygen bonds as well as carbon-carbon double bond remain intact under the reaction conditions. Epoxides also react with thiourea or ammonium thiocyanate in the presence of Mg(HSO 4)2 to afford the corresponding thiiranes in good to excellent yields.
- Salehi, Peyman,Khodaei, Mohammad Mahdi,Zolfigol, Mohammad Ali,Keyvan, Afsaneh
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p. 3041 - 3048
(2007/10/03)
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- LiBF4: A mild and efficient catalyst for conversion of oxiranes to thiiranes with thiourea
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Oxiranes are efficiently converted to the corresponding thiiranes by thiourea in the presence of catalytic amounts of LiBF4 with excellent yields under mild and non-aqueous conditions.
- Kazemi,Kiasat,Ebrahimi
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p. 595 - 600
(2007/10/03)
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- Facile conversion of epoxides to thiiranes with ammonium thiocyanate catalyzed with oxalic acid
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Epoxids are efficiently converted to the corresponding thiiranes by ammonium thiocyanate (NH4SCN) in the presence of catalytic amounts of oxalic acid with excellent isolated yields under mild and nonaqueous reaction condition. This conversion performed under both conventional heating and microwave conditions. Distinct rate enhancement is observed under microwave irradiation.
- Kazemi, Foad,Kiasat, Ali Reza
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p. 1333 - 1337
(2007/10/03)
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- Efficient conversion of epoxides to episulfides with thiourea catalysed with cerium (IV)
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Efficient conversion of epoxides into episulfides with thiourea in the presence of ceric ammonium nitrate (CAN) as catalyst and under mild and non-aqueous conditions is reported; this conversion was performed under both conventional heating and microwave conditions and distinct rate enhancement was observed under microwave irradiation.
- Kazemi,Kiasat
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p. 290 - 291
(2007/10/03)
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- Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-, NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4
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Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN, N3-, NO3-, NO2, SCN, Br and Cl-, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.
- Iranpoor, Nasser,Firouzabadi, Habib,Shekarize, Marzieh
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p. 724 - 727
(2007/10/03)
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- Indium tribromide: A novel and highly efficient reagent for the conversion of oxiranes to thiiranes
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Epoxides react smoothly with potassium thiocyanate in the presence of 5 mol% of indium tribromide under mild and convenient reaction conditions to afford the corresponding thiiranes in high yields. This method is compatible with a wide range of protecting groups and functional groups such as alkenes, alkynes, esters, THP, TBDMS, and PMB ethers present in the molecule.
- Yadav,Reddy,Baishya, Gakul
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p. 396 - 398
(2007/10/03)
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- Mild, efficient, and convenient conversion of oxiranes to thiiranes with ammonium thiocyanate and thiourea in the presence of cerium(IV) polyoxometallate
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Selective conversion of various oxiranes to the corresponding thiiranes in the presence of ammonium thiocyanate and thiourea can be effectively carried out by ammonium decatungestocerate(IV) icosahydrate, (NH4)8 [CeW10O36]·20H2O.
- Mirkhani,Tangestaninejad,Alipanah
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p. 621 - 626
(2007/10/03)
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- Efficient conversion of oxiranes to thiiranes with ammonium thiocyanate catalysed with LiBF4
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Oxiranes are efficiently converted into the corresponding thiiranes by ammonium thiocyanate in the presence of catalytic amounts of LiBF4 in excellent yields under mild and non-aqueous conditions.
- Kazemi,Kiasat,Ebrahim
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p. 176 - 177
(2007/10/03)
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- An expeditious one-pot synthesis of thiiranes from α-halo ketones in solvent-free conditions using microwaves
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Thiiranes are obtained in excellent yields and with high diastereoselectivity upon microwave irradiation of a mixture of α-haloketones, O,O-diethyl hydrogen phosphorodithioate and alumina-supported sodium borohydride in solvent-free conditions.
- Yadav, Lal Dhar S.,Kapoor, Ritu
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p. 2344 - 2346
(2007/10/03)
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