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Paper | Special issue | Vol 88, No. 2, 2014, pp.1191-1200
Published online, 31st October, 2013
DOI: 10.3987/COM-13-S(S)83
Cycloaddition Reactions of Azide, Furan, and Pyrrole Units with Benzynes Generated by the Hexadehydro-Diels–Alder (HDDA) Reaction

Junhua Chen, Beeraiah Baire, and Thomas R. Hoye*

*Department of Chemistry, University of Minnesota, 207 Pleasant Street S. E., Minneapolis, MN 55455, U.S.A.

Abstract

Benzynes can be generated by the intramolecular thermal cycloisomerization of triynes–the title HDDA reaction. We report here that these can be trapped by cycloaddition reaction with trimethylsilyl azide (1,3-dipolar) or a furan or pyrrole (4+2 Diels–Alder).