2-Quinolyl- and 1-isoquinolylnitrenes: ring expansion and ring opening in heteroarylnitrenes.

J Org Chem

Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, Queensland 4072, Australia.

Published: February 2003

Argon matrix photolysis of tetrazolo[1,5-a]quinoline 8 and tetrazolo[5,1-a]isoquinoline 7 causes nitrogen elimination and ring expansion to 1,3-diazabenzo[d]cyclohepta-1,2,4,6-tetraene 13. The photolysis of tetrazolo[5,1-a]isoquinoline 7 also causes ring opening to o-cyanophenylketenimine 22. Mechanisms of ring opening of heteroarylnitrenes are discussed.

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http://dx.doi.org/10.1021/jo026439mDOI Listing

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