Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions of 2,6-Dibenzylidenecyclohexanone and its Derivatives in High-Temperature Water

Xian-Jun Bi A , Luke T. Higham B , Janet L. Scott B and Christopher R. Strauss C D

A Visiting scholar, Chemical and Engineering College, Yunnan Normal University, Kunming 650092, China.

B ARC Special Research Centre for Green Chemistry, Monash University, Clayton VIC 3800, Australia.

C CSIRO Molecular and Health Technologies, Private Bag 10, Clayton South VIC 3169, Australia.

D Corresponding author. Email: chris.strauss@csiro.au

Australian Journal of Chemistry 59(12) 883-886 http://dx.doi.org/10.1071/CH06381
Submitted: 17 October 2006  Accepted: 10 November 2006   Published: 20 December 2006

Abstract

The reactivity of derivatives of 2,6-dibenzylidenecyclohexanone was investigated in water at 220–250°C under microwave conditions, without added catalyst. Retro-Claisen–Schmidt processes predominated. Hydrolytic attack at the benzylic position afforded a 2-benzylidenecyclohexanone derivative and liberated an aryl aldehyde. Dienones substituted with electron-withdrawing or -donating groups on the aryl rings were more susceptible to hydrolysis than was the parent 2,6-dibenzylidenecyclohexanone.


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