Nitrile Oxide Cycloaddition Chemistry Using Benzotriazole as a Steric Auxiliary

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Contents Vol 58(12)

doi:10.1071/CH05189

Nitrile Oxide Cycloaddition Chemistry Using Benzotriazole as a Steric Auxiliary

G. Paul Savage ^A ^B, Gregory T. Wernert ^A

^A CSIRO Molecular and Health Technologies, Clayton South VIC 3169, Australia.
^B Corresponding author. Email: paul.savage@csiro.au





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Australian Journal of Chemistry 58(12) 877–881 http://dx.doi.org/10.1071/CH05189
Submitted: 5 August 2005 Accepted: 30 September 2005 Published online: 20 December 2005

Abstract

The relatively hindered 2,2-bis(benzotriazol-1-yl)acetonitrile oxide was prepared in situ from the precursor hydroximinoyl chloride, and was allowed to react with dipolarophiles to give rise to several isoxazoles. The benzotriazole substituents acted as steric auxiliaries to prevent unwanted dimerization of the nitrile oxide to the furoxan by-product.