Unusual reactions of N-allylic difluoroenamines under thermal conditions

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

doi:10.1039/b309696c

Unusual reactions of N-allylic difluoroenamines under thermal conditions

Chem Commun (Camb). 2003 Dec 7:(23):2902-3. doi: 10.1039/b309696c.

Authors

Hideki Amii¹, Yutaka Ichihara, Takashi Nakagawa, Takeshi Kobayashi, Kenji Uneyama

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan.

PMID: 14680232
DOI: 10.1039/b309696c

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.