"Mechanistic and Preparative Studies of the Intramolecular Photocycliza" by Ken S. Feldman, Jon H. Come et al.
 

Mechanistic and Preparative Studies of the Intramolecular Photocyclization of Methylated 2-(4-Pentenyl) Tropones

Document Type

Article

Publication Date

2-1-1989

Journal / Book Title

The Journal of Organic Chemistry

Abstract

Irradiation of various methylated 2-(4-pentenyl)tropones affords regioisomeric formal[6π+2πand[87π + 2π]cycloadducts. The cyclooctadiene-containing [6π + 2π]adductsare produced as mixtures of stereoisomers. A self-consistent mechanistic scheme based upon evidence accumulated through the study of regioselectivity and stereoselectivity as a function of reaction conditions has been proposed. This mechanism includes several discrete intermediates en route to the final cycloadducts. Attempts to functionalize [6π + 2π] cycloadducts through vinyllithium addition led to unconventional products through unanticipated reaction pathways.

DOI

10.1021/jo00264a017

This document is currently not available here.

Plum Print visual indicator of research metrics
PlumX Metrics
  • Citations
    • Citation Indexes: 32
  • Usage
    • Abstract Views: 5
  • Captures
    • Readers: 2
see details

Share

COinS