Issue 6, 1997

Acid-promoted isomerisation of 1-acceptor-1-sulfenyl-substituted 2-vinylcyclopropanes with C1–C2 bond fission and novel 1,5-sulfenyl rearrangement

Abstract

1-Acceptor-1-sulfenyl-substituted vinylcyclopropanes 1 undergo C1–C2 bond fission and 1,5-sulfenyl rearrangement to give 6-sulfenyl-α,β;γ,δ-unsaturated carboxylic esters and nitriles 4 by treatment with acid. The reactions proceed smoothly by use of a sulfonic acid such as p-TsOH·H2O, CF3SO3H etc. in a non-polar solvent. The results, obtained from reactions of compounds 12 and 16, imply that the C1–C2 bond cleavage and deprotonation from the C2-methyl group of substrates 1 occur via a concerted process. The cross-over experiment showed that the 1,5-sulfenyl shift proceeds intermolecularly. Addition of a catalytic amount of m-MeC6H4SH improves the yield of the rearranged product 4c.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 835-844

Acid-promoted isomerisation of 1-acceptor-1-sulfenyl-substituted 2-vinylcyclopropanes with C1–C2 bond fission and novel 1,5-sulfenyl rearrangement

T. Iwama, H. Matsumoto and T. Kataoka, J. Chem. Soc., Perkin Trans. 1, 1997, 835 DOI: 10.1039/A606579A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements