Isoxazole to oxazole: a mild and unexpected transformation

Jones, Ray; Chatterley, Alexander; Marty, Romain; Owton, W. Martin; Elsegood, Mark

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Isoxazole to oxazole: a mild and unexpected transformation

journal contribution

posted on 2015-02-27, 11:02 authored by Ray Jones, Alexander Chatterley, Romain Marty, W. Martin Owton, Mark ElsegoodMark Elsegood

3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.

History

School

Science

Department

Chemistry

Published in

CHEMICAL COMMUNICATIONS

Volume

51

Issue

6

Pages

1112 - 1115 (4)

Citation

JONES, R.C.F. ... et al., 2015. Isoxazole to oxazole: a mild and unexpected transformation. Chemical Communications, 51 (6), pp. 1112 - 1115.

Publisher

Royal Society of Chemistry

Version

VoR (Version of Record)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution 3.0 Unported (CC BY 3.0) licence. Full details of this licence are available at: http://creativecommons.org/licenses/by/3.0/