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■ Chemistry of Azidoquinones. Synthesis and Thermolysis of the Azido-o-quinone, 3-Azido-4-(4-methylcyclohexa-3,6-dione-1,4-dienyl)-1,2-naphthoquinone

Steward P. Lee and Harold W. Moore

*Department of Chemistrym University of California, One Shields Avenue, Davis, CA 95616-5295, U.S.A.

Abstract

The synthesis and thermal decomposition of 3-azido-4-(4-methylcyclohexa-3,6-dione-1,4-dienyl)1,2-naphthoquinone (7) is reported. This is the first example of the thermal chemistry of an azido-o-quinone and is shown to undergo facile ring closure to the carbazolebisquinone 9. Analogous ring closures were observed for the hydroquinone derivatives of 7, i.e., 10a and 10b.