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Communication | Regular issue | Vol 23, No. 4, 1985, pp.813-818
Published online, 1st January, 1970
DOI: 10.3987/R-1985-04-0813
Azabiocyclo[3.2.0]heptane-3,4-dione (10): A Thermal Azonia 1,3-Shift of 2-Azabicyclo[3.2.0]hept-2-enes to 2-Azanorborn-2-enes

Takehiro Sano,* Kazuhiko Tanaka, Yoshie Horiguchi, and Yoshisuke Tsuda

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

Abstract

Thermolysis of 2-azabicyclo[3.2.0]hept-2-enes caused azonia 1,3-shift in non-stereospecific manner to give 2-azanorborn-2-enes. This rearrangement reaction was greatly affected by the stereochemistry of the substituent at the migrating center.