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ChemInform Abstract: Acid-Promoted Isomerization of 1-Acceptor-1-Sulfenyl-Substituted 2- Vinylcyclopropanes with C1-C2 Bond Fission and Novel 1,5-Sulfenyl Rearrangement.

✍ Scribed by T. IWAMA; H. MATSUMOTO; T. KATAOKA

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199733060

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✦ Synopsis

The title reactions of compounds (III) result in α,β;γ ,δ-unsaturated carboxylic esters and nitriles (IV). The reactions proceed by use of a sulfonic acid such as TosOH, TfOH etc. in a non-polar solvent. Addition of a catalytic amount of m-MeC6H4SH improves the yield of product (VI). The mechanism of the bond cleavage and deprotonation from the C2-methyl group is a concerted one; the 1,5-sulfenyl shift is an intermolecular process. -

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