Synthetic studies on O-heterocycles via cycloadditions. Part 1. Photochemical (electron transfer sensitised) C-C cleavage of diaryloxiranes
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 153-157
- https://doi.org/10.1039/p19900000153
Abstract
Irradiation of trans-stilbene oxide with naphthalene-1,4-dicarbonitrile as sensitiser in the presence of electron deficient dipolarophiles leads, via a presumed carbonyl ylide, to various dihydro- and tetrahydro-furans. This chemistry is extended, for the first time, to an example with both aryl rings oxygenated, 2,3-bis(p-methoxyphenyl)oxirane, using anthracene-9,10-dicarbonitrile as sensitiser; in contrast to stilbene oxide, in this case direct irradiation, triplet sensitisation, or thermal activation lead to C–O bond cleavage. The bis(p-methoxyphenyl) adducts, of interest in the lignan area, are formed with a lack of stereoselectivity suggestive of diradical intermediates.This publication has 2 references indexed in Scilit:
- Lignans from aegilops ovata L.Tetrahedron, 1979
- Vier neue lignane aus aptosimum spinescens ( Thunbg. )Tetrahedron Letters, 1976