Treating N-substituted pyrrolidines and piperidines bearing an allylic chain to the nitrogen with strong bases leads to the opening of the heterocycle and provides 1,3-dienes disubstituted with an alkoxy and an aminoalkyl chain. The effects of the base and the solvent have been studied, as well as the influence of the ring size and the nitrogen substituent. The results obtained suggest a possible pre-chelation of the base cation before the deprotonation
Pyrrolidinic and Piperidinic Ring Fission by Conjugated Elimination
VENTURELLO, Paolo;
2002-01-01
Abstract
Treating N-substituted pyrrolidines and piperidines bearing an allylic chain to the nitrogen with strong bases leads to the opening of the heterocycle and provides 1,3-dienes disubstituted with an alkoxy and an aminoalkyl chain. The effects of the base and the solvent have been studied, as well as the influence of the ring size and the nitrogen substituent. The results obtained suggest a possible pre-chelation of the base cation before the deprotonation
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