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Org Lett. 2002 May 02;4(9):1487-9. doi: 10.1021/ol025693y.

Photochemistry of benzotriazole: an unprecedented tautomer-selective intermolecular [2+2] photocycloaddition.

Organic letters

Kevin I Booker-Milburn, Paul M Wood, Richard F Dainty, Michael W Urquhart, Andrew J White, Helen J Lyon, Jonathan P H Charmant

Affiliations

  1. School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. [email protected]

PMID: 11975610 DOI: 10.1021/ol025693y

Abstract

[reaction: see text]. Irradiation of benzotriazole with a variety of maleimide derivatives leads to the stereo- and regioselective formation of aryl [2 + 2] photocycloaddition products. Further studies with 2-alkyl benzotriazole derivatives indicates that in the case of the parent benzotriazole this cycloaddition proceeds selectively via the 2H-tautomer.

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