CYCLOPROPANONES VI. REACTION OF CYCLOPROPANONE WITH AMINES*

(Received 23 hay 1967) Wasserman and Clagettl have reported that the reaction of l-ethoxy-l-hydroxycyclopropane with aniline at room temperature yields l,l-dianilinocyclo-propane (2). These workers proposed that cyclopropanone (1 and l-anilino-l- $ hydroxycyclopropane (3 may be intermediates in the formation of 6. The results reported here are pertinent to the above report and the general field of cyclo-propanone and cyclopropane chemistry. 2-6 Treatment of methylene chloride solutions7 of cyclopropanone (3 with 1.0 equivalent of aniline at-78 ’ results in immediate formation of a mixture of two compounds, $ (33%) ad 2 (66%). Treatment of&with two equivalents of aniline under similar conditions results in formation of aas major product (95%) and 2 (a