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Gilman-Cason Ketone Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr271

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Gilman-Cason Ketone Synthesis. Comprehensive Organic Name Reactions and Reagents. 271:1230–1233.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of ketones from alkyl (or aryl) cadmium and acyl chloride or anhydride is generally referred to as the Gilman–Cason ketone synthesis. In this reaction, the cadmium reagent is preferentially prepared from a lithium derivative rather than a Grignard reagent, although the aromatic Grignard reagents form cadmium derivatives readily and give good yields of aromatic ketones. It has been reported that alkyl cadmium can dissociate and form alkyl radical upon heating. This reaction can be used in the synthesis of ketones with multifunctional groups, including carbonyl and esters.

Keywords:

  • Grignard reagents;
  • acyl halides;
  • butenylcadmium reagent;
  • alkyl cadmium