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Paper | Regular issue | Vol 24, No. 3, 1986, pp.687-696
Published online, 1st January, 1970
DOI: 10.3987/R-1986-03-0687
Dynamic 13C N.M.R. Studies of Electrochemically Formed 4a-N’ and 4a-4a’ Dehydrodimers of 1,2,3,4-Tetrahydrocarbazole

James M. Bobbitt,* Thomas T. -t. Chou, and Thomas K. Leipert

*Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, U.S.A.

Abstract

The electrochemical oxidation of 1,2,3,4-tetrahydrocarbazole in strong base (KOCH3 in CH3OH) at a potential of + 0.15 V (vs S.C.E.) on a graphite felt anode produced a series of dehydrodimers having interesting stereochemical and 13C dynamic N.M.R. properties. The 4a-N’ dimer was isolated as a pair of atropisomers due to restricted rotation around a nitrogen-sp3 carbon bond. Meso and dl forms of the 4a-4a’ dimer were also isolated. Low temperature 13C N.M.R. spectra of the 4a-4a’ dimers showed that they represent a unique case of stereochemistry when rotation is restricted. The case corresponds to a situation where the anti conformation around an acyclic sp3-sp3 carbon-carbon bond is forbidden, and only the two gauche forms are present.