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Paper | Special issue | Vol 30, No. 2, 1990, pp.1131-1140
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S112
Organic Nitrosonium Salts. II. Stability Studies and Oxidations of Some Indole Derivatives

James M. Bobbitt, M. Cecile Flores Guttermuth, Zhenkun Ma, and Huitong Tang

*Department of Chemistry, U-60, Rm.151, 215 Glenbrok Rd., University of Connecticut, Storrs, CT 06269-3060, U.S.A.

Abstract

The stabilities of various salts of the 2,2,6,6-tetramethylpiperidine-1-oxonium ion were studied. 2,2,6,6-Tetramethylpiperidine-1-oxonium tetrafluoroborate was shown to react with 1,2,3,4-tetrahydrocarbazole (1-H-2,3,4,9-tetrahydrocarbazole) to give, in the presence of water, 4-keto-1,2,3,4-tetrahydrocarbazole in good yield. Under the same conditions, cyclopent[b]indole and cyclohept[b]indole gave the corresponding keto derivatives. In the absence of water, the oxidation of tetrahydrocarbazole gave a mixture of dimers, probably derived from the Diels-Alder self condensation of 1-H-2,3-dihydrocarbazole. The condensation is reversible and, in acid, the dimer mixture gives a salt of 1-H-2,3-dihydrocarbazole which can be reduced with sodium borohydride to give back tetrahydrocarbazole.