- Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions
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Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.
- Li, Jiaming,Li, Jian,Ji, Xiaoliang,He, Runfa,Liu, Yang,Chen, Zebin,Huang, Yubing,Liu, Qiang,Li, Yibiao
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supporting information
p. 7412 - 7417
(2021/10/01)
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- Mild and efficient desulfurization of thiiranes with MoCl5/Zn system
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Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.
- Lee, Yeong Jin,Shin, Jeong Won,Yoo, Byung Woo
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- Convenient synthesis of 1,3-dithiolane-2-thiones: Cyclic trithiocarbonates as conformational locks
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A series of novel 1,3-dithiolane-2-thiones, or cyclic trithiocarbonates, has been prepared by a new simple procedure: a treatment of the corresponding epoxides with the commercially available potassium ethyl xanthogenate, KSC(S)OEt. The stereochemistry of the products was determined by 1H NMR and in some cases by single-crystal X-ray data. Cyclohexane-based 1,3- dithiolane-2-thiones revealed a trans-fusion of the carbo- and hetero-cycles. The products obtained from the mono-substituted cyclohexene oxides demonstrated an axial position of the substituents. Thus the epoxide transformation into trithiocarbonate can be used as a method for locking cyclic compounds in unstable conformations.ARKAT-USA, Inc.
- Dotsenko, Irina A.,Zhao, Qinliang,Franz, Andreas H.,Batoon, Patrick,Samoshina, Nataliya M.,Samoshin, Vyacheslav V.
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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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- 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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- A facile and efficient one-pot synthesis of thiirans by the reaction of benzoxazolyl β-ketosulfides with NaBH4/NaOH
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Convenient and efficient procedures for thiirans have been developed via a one-pot reaction of benzoxazolyl β-ketosulfides with NaBH4 and NaOH in MeOH and THF. The reaction is considered to proceed via the spiro intermediate by the ipso-additio
- Yamada, Nobuhiko,Mizuochi, Masayoshi,Takeda, Masahiro,Kawaguchi, Hiroyuki,Morita, Hiroyuki
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p. 1166 - 1168
(2008/09/18)
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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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- Iodine as a mild, efficient, and cost-effective catalyst for the synthesis of thiiranes from oxiranes
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We developed an efficient protocol for the synthesis of thiiranes from oxiranes using a catalytic amount of molecular iodine. The notable features of this procedure are mild reaction conditions, high conversions, short reaction times, economic viability o
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Sengupta, Sandip,Gupta, Manoj K.,Baishya, Gakul,Harshavardhana, Sukkala J.,Dash, Uttam
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experimental part
p. 1363 - 1367
(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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- 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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- 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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- [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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- A convenient synthesis of episulfides and their conversion into alkenes
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A convenient and stereoselective synthesis of episulfides based on the reaction of readily available S-(β-oxoalkyl) thiophosphate with sodium borohydride and their conversion into alkenes is described.
- Dybowski, Piotr,Skowrońska, Aleksandra
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p. 1134 - 1136
(2007/10/03)
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- ELECTROCHEMICAL REDUCTION OF α,α'-DIBROMO-DIBENZYLSULFONE, -SULFOXIDE, AND -SULFIDE
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The electrochemical reduction of the title compounds in dimethylformamide affords in all cases stilbene as a major product, leading to the conclusion that cyclization to a three-membered ring containing sulfur is a common feature in these reductions.Other products isolated in the reductions help to shed light upon the course of the reactions.
- Fry, Albert J.,Ankner, Kjell,Handa, Vijay
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p. 1791 - 1794
(2007/10/02)
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- Flash Vacuum Pyrolysis of 1,3-Oxathiolan-5-ones
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Flash vacuum pyrolysis of 1,3-oxathiolan-5-ones causes loss of carbon dioxide with the concominant formation of the corresponding thiiranes in nearly quantitative yield.The reaction is stereospecific and proceeds by clean inversion of configuration.This suggests a concerted loss of carbon dioxide.Furthermore, substituent effects strongly support the intermediacy of thiocarbonyl ylides.Consequently, this method becomes one of the simplest ways of generating these species.
- Cameron, Tim B.,Pinnick, Harold W.
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p. 744 - 747
(2007/10/02)
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- Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVII. - Conversion of 2-Methylimino-1,3-oxathiolanes into Thiiranes
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2-Methylimino-1,3-oxathiolanes 3, readily obtained from lithiated S,S'-dialkyl N-(methyl)imidodithiocarbonates 1 and carbonyl compounds 2, were transformed into thiiranes 6 via N,N-dimethyl-N-(1,3-oxathiolan-2-ylidene)ammonium iodides 7.With exclusion of 5-aryl-substituted compounds 3 the reaction proceeds highly diastereoselectively.
- Hoppe, Dieter,Follmann, Rainer
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p. 1779 - 1785
(2007/10/02)
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