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 https://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.


Acknowledgments

We thank Angela Ziebell and Dr Ulf Kreher for conducting a preliminary experiment, Anthony Rosamilia for providing a sample of 2b, the Australian Research Council (ARC) for funding this research through the ARC Special Research Centre for Green Chemistry, and an Australian Postgraduate Award (to L.T.H.), The People’s Republic of China for supporting sabbatical leave (for X.J.B.), and Milestone (Italy) for the loan of microwave reactors and ancillary equipment. Drs Carl Braybrook and Jo Cosgriff of CSIRO Molecular & Health Technologies are thanked for performing GC-MS analyses.


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