Triplet di-π-methane rearrangement of a ‘free-rotor’ 2-prop-2-enylcyclopent-2-enone

1 January 1972

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 15,p. 864-865
https://doi.org/10.1039/c39720000864

Abstract

The 2-prop-2-enylcyclopent-2-enone (1) undergoes an inefficient triplet di-π-methane rearrangement to give (2) whereas the side-chain substituted analogue (4), under similar conditions, undergoes only Z–E-isomerisation; the reactivity differences are rationalised on the basis of dissipation of triplet energy by ‘free-rotor’ effects.

Keywords

METHANE