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Retropinacol Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr535

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Retropinacol Rearrangement. Comprehensive Organic Name Reactions and Reagents. 535:2378–2381.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is the conversion of alcohols with a tertiary β-carbon into olefin along with the migration of an alkyl group from the tertiary β-carbon in the presence of an acid. This reaction is generally known as the retropinacol rearrangement. The extent of the rearrangement is determined by the strength of the base and the accessibility of the β-position to the base, so that shielding the β-carbon by either a bulky group or an electron-rich group can prevent the retropinacol rearrangement. The modification of reaction takes place via base triggered retropinacol rearrangement, by the use of 2-chloro-1,1,2-trifluoroethyldiethylamine. This reaction has been found useful in organic synthesis.

Keywords:

  • tertiary β-carbon;
  • pinacolone;
  • conjugate base;
  • electron-rich group