Strain-Induced Transformations of Bicyclo[3.1.0]hex-1-enes

Abstract

Bicyclo[3.1.0]hex-1-ene is a highly strained bicyclic intermediate that generates trimethylenemethane (TMM) diradical through breaking the C–C bond of its methylene cyclopropane moiety. The reactivity of bicyclo[3.1.0]hex-1-enes and trimethylenemethane (TMM) diradicals depend on the reaction temperature and substitution patterns. This short review covers various strain-induced transformations of bicyclo[3.1.0]hex-1-enes and their formal [3+2] cycloadditions through TMM diradicals and presents synthetic applications to natural products containing triquinane and tropone structures.

1 Introduction

2 Early Reports on Bicyclo[3.1.0]hex-1-enes

3 Approaches to Form Bicyclo[3.1.0]hex-1-enes

4 Structure and Reactivity of Bicyclo[3.1.0]hex-1-enes

4.1 Isomerization

4.2 Dimerization

4.3 [3+2] Cycloaddition

4.4 [4+2] Cycloaddition

5 Synthetic Applications to Natural Products

6 Summary and Outlook

Key words

bicyclo[3.1.0]hex-1-enes - TMM diradical - dimerization - [3+2] cycloaddition - triquinanes

Publication History

Received: 26 June 2021

Accepted after revision: 26 July 2021

Article published online:
20 August 2021

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