Synthesis 2003(13): 2079-2083
DOI: 10.1055/s-2003-41038
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Practical Synthesis of Mixed Allyl and Allenesulfinates

Samuel Braverman*, Tatiana Pechenick
Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel
Fax: +972(3)5351250; e-Mail: bravers@mail.biu.ac.il;
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Publikationsverlauf

Received 6 May 2003
Publikationsdatum:
28. August 2003 (online)

Abstract

A new, general, and efficient method for the preparation of mixed sulfoxylates (ROSOR′) by treatment of symmetrical dialkoxy disulfides (ROSSOR) with alcohols at room temperature has been found. Subsequent spontaneous [2,3]-sigmatropic rearrangements of mixed sulfoxylates such as alkyl allyl and alkyl propargyl sulfoxylates afford mixed alkyl allyl and alkyl allenesulfinates in good yield. The latter are not readily available by other routes.

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