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Paper | Regular issue | Vol 53, No. 1, 2000, pp.151-158
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8747
Anionic [3,3] Rearrangements of Cyclic Hydrazine Diacylates to Medium-Size Cyclic Diamides and Their Structures

Yasuyuki Endo,* Takuya Uchida, and Kentaro Yamaguchi

*Graduate School of Pharmaceutical Science, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan


The anionic rearrangement of N,N’-dimethyl-N,N’-diacylhydrazines to 1,2-disubstituted succinamides proceeds in the presence of a ajacent enolate- stabilizing substituent such as a phenyl group. However, a substituent that poorly stabilizes the α-carbanion results in an extremely low yield of the products. The [3,3] sigmatropic rearrangement generally requires a chair form for the cyclic six-centered transition state. When the dienolates of N,N’-diacylhydrazines have favorable steric factors for the cyclic transition state, the rearrangement seems to proceed smoothly. The diacylates of 5- to 8-membered cyclic hydrazine which readily adopt a favorable conformation for the [3,3] rearrangement readily rearrange to 9- to 12-membered cyclic diamides.