Issue 0, 1986

Structural influences on the isomerization of 4-benzyl- and 4-allyl-1,2-naphthoquinones to quinonemethides and their stereochemistry

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 1627-1631

Structural influences on the isomerization of 4-benzyl- and 4-allyl-1,2-naphthoquinones to quinonemethides and their stereochemistry

A. Takuwa, H. Iwamoto, O. Soga and K. Maruyama, J. Chem. Soc., Perkin Trans. 1, 1986, 1627 DOI: 10.1039/P19860001627

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