1996•Phosphorus, sulfur, and silicon and the related elementsRequires access

SIGMATROPIC-[2,3]-WITTIG REARRANGEMENT OF α-ALLYLIC-HETEROSUBSTITUTED METHYLPHOSPHONATES. REARRANGEMENT IN THE SULFUR SERIES

Hubert Makomo, Serge Masson, Didier Putman, Monique Saquet, Fabrice G. Siméon, Elie About‐Jaudet, Noël Collignon

Abstract

The diisopropyl (allylthiomethyl)phosphonates (variously substituted on the allylic group) are submitted to the [2,3]-sigmatropic rearrangement, via either the carbanions or the sulfonium ylides. Synthetic potentialities are examined, and in particular new (1-mercaptobut-3-enyl)phosphonates are conveniently prepared.

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Available abstract

Key concepts: Allylic rearrangement, Sigmatropic reaction, Carbanion, Sulfonium, Carroll rearrangement, Chemistry, Sulfur, Claisen rearrangement