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Communication | Regular issue | Vol 22, No. 1, 1984, pp.53-58
Published online, 1st January, 1970
DOI: 10.3987/R-1984-01-0053
2-Azabicyclo[3.2.0]heptane-3,4-dione (8): A Novel Acid Catalyzed Skeletal Rearrangement of 7-Oxy-7-vinyl Derivatives to 2-Azatricyclo[,9]nonane-3,7-diones

Takehiro Sano,* Jun Toda, and Yoshisuke Tsuda

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


Treatment of 7-trimethylsilylaxy-7-vinyl-2-azabicyclo[3.2.0]heptane-3,4-diones with various acids yielded novel caged compounds, 2-azabicyclo[,9]nonane-3,7-diones, whose formation is explained in terms of intramolecular Prins type cyclization with concomitant 1,2-shift.