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Nierenstein Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr463

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Nierenstein Reaction. Comprehensive Organic Name Reactions and Reagents. 463:2058–2061.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of α-chloromethyl ketone by treatment of an aliphatic or aromatic acyl chloride with diazomethane is generally known as the Nierenstein reaction. This reaction can be used to make other reactive halides carrying different elements (e.g., mercury) and even molecules containing a halogen sensitive group, such as Si-H link. The direct product from such reaction is a diazoketone. It has been reported that in situ generated diazoketones decompose and produce a variety of products. This reaction works poorly for preparing α-bromomethyl ketone, probably because the bromine atom is less mobile. Under certain conditions, the dihalogenated dioxanes are also produced. This reaction has been extended to a one-pot preparation of terminal olefins.

Keywords:

  • diazoketone;
  • benzoyl chloride;
  • α-chloromethyl ketones;
  • phenylacetyl chloride