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The reaction of stable phosphorus ylides with elemental sulfur. Formation of olefins; cis-trans selectivity

✍ Scribed by Kentaro Okuma; Tomoko Ishida; Shinya Morita; Hiroshi Ohta; Tohru Inoue

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 524 KB
Volume: 6
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520060312

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✦ Synopsis

Metal and temperature effects on thio-Wittig reactions have been studied. Stabilized phosphorus ylides, such as carbomethoxymethylenetriphenylphosphorane, reacted with sulfur to afford dimethyl maleate and dimethyl fumarate in a 1 : 4 ratio. As in the case of conventional Wittig reactions with semistabilized ylides, it has been shown that the stereochemistry (E 1 Z ratio) of alkene formation is determined at the point that a new carbon-carbon bond has been formed to give a thiaphosphetane intermediate. The temperature dependence of this reaction is also discussed.

We first carried out the reaction of carbomethoxymethylentriphenylphosphorane (la) with elemental sulfur under a variety of conditions. The solvents used in this reaction were toluene and tet-

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