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Communication | Regular issue | Vol 16, No. 3, 1981, pp.355-358
Published online, 1st January, 1970
DOI: 10.3987/R-1981-03-0355
2-Azabicyclo[3.2.0]heptane-3,4-diones (1). A Novel Epimerization Reaction of C7-Substitutents

Takehiro Sano,* Yoshie Horiguchi, and Yoshisuke Tsuda

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


On treatment with bases, 7,7-disubstituted and 7-substituted 2- azabicyclo[3.2.0]heptane-3,4-diones rapidly epimerized at C7 to give a themodynamically more stable isomer (7-endo isomer in the cases of mono-substituted compounds) predominantly, then changed into dihydroazatropolones. The mechanism of this novel epimerization reaction was suggested as a homolytic cleavage and recombination of C1-C7 bond, which may be of a thermal process accelerated by formation of an anion on the adjacent nitrogen.