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Schmidt-Rutz Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr567

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Schmidt-Rutz Reaction. Comprehensive Organic Name Reactions and Reagents. 567:2511–2513.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of nitroolefins by means of the treatment of acetates of α-nitro-alcohols with sodium bicarbonate is generally known as the Schmidt–Rutz reaction. This reaction is also referred to as the Schmidt–Rutz degradation. The Schmidt–Rutz reaction is applicable to the substrates without any other base-labile functional groups and usually gives nitro-olefins in good yields. It has been reported that the best yields can be achieved from the esters of nitro-alcohols with nine or more than nine carbon atoms. The resulting nitro-olefins can be reduced to amines, so that the Schmidt–Rutz reaction has become one of the powerful methods for amines with a definite structure free of isomers. Moreover, this reaction has been widely used in carbohydrate chemistry, due to a good crystalline capability of nitro carbohydrate.

Keywords:

  • α-nitro esters;
  • α-carbon bonding;
  • sodium bicarbonate;
  • carbohydrate acetates