Abstract A convenient method for the oxysulfenylation of alkenes using dimethyl sulfoxide/oxalyl chloride is described. Cycloalkenes give trans-adducts stereospecifically. The reactions of styrene are highly regioselective for Markovnikov adducts, whereas aliphatic alkenes lead to anti-Markovnikov adducts mainly. Graphical Abstract
Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S−S Bond
作者:Nobukazu Taniguchi
DOI:10.1021/jo060834l
日期:2006.9.1
Copper-catalyzed 1,2-hydroxysulfenylation of alkenes can be carried out by the use of disulfides and acetic acid in air. This reaction regio- and anti-selectively gave the corresponding 1,2-acetoxysulfides. Furthermore, the present method enables the use of both organosulfide groups of disulfide.
The generation and properties of episulfonium intermediates. 8. Regioselectivity in the nucleophilic ring opening of episulfonium ion derivatives of some unsymmetrical alkyl- and arylolefins
作者:A. S. Gybin、V. A. Smit、V. S. Bogdanov、M. Z. Krimer