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Lombardo Methylenation

(Lombardo Olefination, Lombardo Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr397

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Lombardo Methylenation. Comprehensive Organic Name Reactions and Reagents. 397:1767–1771.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The modification of the Takai–Nozaki methylenation (also known as the Nozaki–Hayashe methylenation) to convert ketones/aldehydes into alkenes using the “low temperature aged” carbenoid reagent generated from zinc, dibromomethane, and TiCl4 is referred to as the Lombardo methylenation and the combination of Zn/CH2Br2/TiCl4 is known as the Lombardo reagent. Several features of this reaction have been presented and compare them against the Wittig reaction. Besides this many disadvantages of the reaction have also been discussed. This reaction has been widely used for the methylenation of carbonyl functionality.

Keywords:

  • dibromomethane;
  • TiCl4;
  • β,γ-unsaturated enones;
  • zinc