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de Mayo Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr183

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. de Mayo Reaction. Comprehensive Organic Name Reactions and Reagents. 183:858–861.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is a two-step process involving the [2+2] photocycloaddition of an enol of a 1,3-dicarbonyl compound with an olefin to form a cyclobutanol intermediate and the retro aldol condensation of such a cyclobutanol to give 1,5-dicarbonyl compounds and is known as the de Mayo reaction. It has been reported that in the absence of extreme steric hindrance, the regiochemistry of cycloaddition is predictable, and such regioselectivity is affected by a solvent. When an electron-deficient, polarized olefin (CH2[DOUBLE BOND]CHR, R [DOUBLE BOND] CN, Cl, COCH3, CO2CH3, etc) is subjected to the [2+2] photocycloaddition with enol of 1,3-dicarbonyl compound, the so-called head-to-tail regioisomer with exo-orientation of R on such an olefin is the favored product.

Keywords:

  • [2+2] photocycloaddition;
  • β-keto esters;
  • cyclic 1,3-dicarbonyl compound;
  • cyclooctanedione