Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine

Assignment by Cottle and co-workers of the cyclopropanol structure to one of the products of the reaction of ethylmagnesium bromide with epichlorohydrin has been verified by an independent synthesis from cyclopropylmagnesium chloride. Cyclopropyl acetate and p-toluenesulfonate have been prepared and characterized. Cyclopropyl bromide has been obtained from the reaction of silver cyclopropanecarboxylate with bromine. The von Braun reaction between N-cyclopropylbenzamide and phosphorus pentabromide was unsuccessful. The Beckmann rearrangement of cyclopropyl methyl ketoxime has been investigated as part of a synthesis of cyclopropylamine