Reaction of the 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole 1 with organomagnesium halides in the presence of Cu2Cl2 forms only the cis-4a,9a-dialkylhexahydrocarbazole derivatives 2 through a radical mechanism. Characterization of the cis-ring junction formation was confirmed by the alkylation of an η6-tricarbonylchromium complex of the 4a-methyl derivative 1.
J. G. Rodríguez and A. Urrutia, J. Chem. Soc., Perkin Trans. 1, 1995, 665 DOI: 10.1039/P19950000665
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