- Green synthesis of vicinal dithioethers and alkenyl thioethers from the reaction of alkynes and thiols in water
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The reaction of a wide range of alkynes with thiols to give vicinal dithioethers in water, under mild conditions, is reported. In addition, non-terminal propargyl alcohols react with aryl thiols in water to produce a highly regio-and stereoselective monohydrothiolation product, (E)-alkenyl thioether. Reaction mechanism and computational studies on the selectivity of the product are presented.
- Jin, Zhuang,Xu, Bo,Hammond, Gerald B.
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supporting information; experimental part
p. 168 - 173
(2010/03/24)
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- Convenient method for the addition of disulfides to alkenes
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Catalytic disulfenylation reaction of alkenes by common Lewis acids has been investigated in detail. While reactions by FeCl3 were feasible with cycloalkenes and other simple alkenes, much faster and excellent conversions were possible by AlCl
- Yamagiwa, Noriyuki,Suto, Yutaka,Torisawa, Yasuhiro
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p. 6197 - 6201
(2008/03/14)
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- HIGHLY SELECTIVE THIOSELENATION OF OLEFINS USING DISULFIDE-DISELENIDE MIXED SYSTEM
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A highly selective thioselenation of olefins has been attained by using a disulfide-diselenide mixed system.
- Ogawa, Akiya,Sonoda, Noboru
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p. 331 - 332
(2007/10/02)
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- 1,2-Disulphenylation of Alkenes Induces by a Hypervalent Iodine(III) Reagent
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Addition of diphenyl disulphide and dimethyl disulphide to alkenes successfully proceeded with to give high yields of 1,2-bis(phenylthio)alkanes and 1,2-bis(methylthio)alkanes, respectively.
- Kitamura, Tsugio,Matsuyuki, Jun-ichi,Taniguchi, Hiroshi
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p. 1607 - 1608
(2007/10/02)
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- BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES
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The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.
- Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
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p. 1145 - 1156
(2007/10/02)
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