Unusual reactions of N-allylic difluoroenamines under thermal conditions

Literature Information

Publication Date 2003-10-20
DOI 10.1039/B309696C
Impact Factor 6.222
Authors

Hideki Amii, Yutaka Ichihara, Takashi Nakagawa, Takeshi Kobayashi, Kenji Uneyama


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Abstract

N-Allylic difluoroenamines exhibited unusual behaviors under thermal conditions; N-allyl difluoroenamines in refluxing xylene afforded not only aza-Claisen rearrangement products, but also 2-azabicyclo[2.1.1]hexanes, whose formation could be explained via intramolecular [2+2]-cycloaddition, whilst N-prenyl difluoroenamine underwent an ene reaction to give the pyrrolidine as a sole product.

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