Structural influences on the isomerization of 4-benzyl- and 4-allyl-1,2-naphthoquinones to quinonemethides and their stereochemistry
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 1627-1631
- https://doi.org/10.1039/p19860001627
Abstract
The isomerization of 4-benzyl-1,2-naphthoquinones and 4-allyl-1,2-naphthoquinones to quinonemethides has been studied. The steric interaction and extra π conjugation in the quinonemethide, and acidity of methylene protons of the quinone, are controlling factors for the isomerization. 1H N.m.r. studies suggested that the quinonemethides have the E configuration.This publication has 1 reference indexed in Scilit:
- Reactions of 1,2-naphthoquinones with allyltrialkyltinsThe Journal of Organic Chemistry, 1984