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Di-Π-Methane Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr195

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Di-Π-Methane Rearrangement. Comprehensive Organic Name Reactions and Reagents. 195:910–915.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction, known as the Zimmerman rearrangement, di-π-methane rearrangement, di-π-methane photorearrangement, or di-π-methane reaction, is a photochemical reaction of a molecular entity comprising two π-systems separated by a saturated carbon atom (a sp3 carbon, e.g. a methylene group) involving the migration of one π-moiety bonded to the saturated carbon to other π-moiety accompanied by the concomitant formation of a cyclopropane ring from the remaining π-moiety and methylene group. This rearrangement has been reported to consist at least six versions and all these variants differ from each other. This rearrangement has high regiospecificity with a strong preference for migration of the less conjugated π-moiety to the more conjugated one. This rearrangement has proven valuable in preparation of substituted cyclopropanes.

Keywords:

  • oxa-di-π-methane rearrangement;
  • arylvinylmethane;
  • plasma;
  • aza-di-π-methane rearrangement