Fischer Phenylhydrazone and Osazone Synthesis
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Fischer Phenylhydrazone and Osazone Synthesis. Comprehensive Organic Name Reactions and Reagents. 236:1083–1087.
- Published Online: 15 SEP 2010
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The condensation between phenylhydrazine and a carbonyl compound (aldehyde or ketone) to form phenylhydrazone and the compounds condensed from carbohydrates and 2 eq of phenylhydrazine are generally known as osazones or specifically referred to as glycosazones. These reactions are known as Fischer phenylhydrazone and osazone synthesis. The glycosazones have been employed to elucidate the configuration of sugars. It has been found that the phenylhydrazones of aliphatic ketones and aldehydes rapidly tautomerize to the more stable azo isomers in solution and glycosazones of carbohydrates exist as chelated acyclic forms. This reaction has general application in the preparation of phenylhydrazones of carbonyl compounds and osazone derivatives of carbohydrates.
- acyclic osazone;