학술논문
General photoisomerization approach to trans-benzobicyclo(5.1.0)octenes: synthetic and mechanistic studies
Document Type
Academic Journal
Source
Journal of Organic Chemistry. Nov 4, 1994, Vol. 59 Issue 22, p6652, 15 p.
Subject
Language
ISSN
0022-3263
Abstract
A new photochemical pathway helps prepare strained trans-benzobicyclo(5.1.0)octene ring systems. Primary photochemical events associated with benzannulated substrates reveal the presence of photostationary states between cis- and trans-fused cyclopropanes. The primary reaction pathway is the cleavage of the peripheral benzylic cyclopropane bonds. Quenching experiments with piperylene confirm the domination of triplet diradical intermediates in the trans-to-cis conversions, and controlled reaction conditions improve methods for preparative isomerizations.