Rearrangement of 2-aryl-3, 3-dichloroazetidines: intermediacy of 2-azetines

Y Dejaegher, S Mangelinckx…

Index: Dejaegher, Yves; Mangelinckx, Sven; De Kimpe, Norbert Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2075 - 2081

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Citation Number: 53

Abstract

An easy synthesis of 2-aryl-3, 3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3, 3-dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2+ 2] cycloaddition. The reactivity of 3, 3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy (aryl) methyl] aziridines by ring ...