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

Corresponding Author

Kentaro Okuma

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, JapanSearch for more papers by this author

Tomoko Ishida,

Tomoko Ishida

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Shinya Morita,

Shinya Morita

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Hiroshi Ohta,

Hiroshi Ohta

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Tohru Inoue,

Tohru Inoue

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Kentaro Okuma,

Corresponding Author

Kentaro Okuma

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, JapanSearch for more papers by this author

Tomoko Ishida,

Tomoko Ishida

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Shinya Morita,

Shinya Morita

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Hiroshi Ohta,

Hiroshi Ohta

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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Tohru Inoue,

Tohru Inoue

Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-01, Japan

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First published: May/June 1995

https://doi.org/10.1002/hc.520060312

Citations: 6

^†

Dedicated to Prof. Shigeru Oae on the occasion of his seventy-fifth birthday.

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Abstract

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: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.

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

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

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