Cyclopropane Derivatives. II. The Electric Moments of Some Alicyclic Compounds

Abstract

There is considerable evidence that compounds in which a cyclopropane ring is located adjacent to an unsaturated linkage, such as a carbonyl group or double bond, exhibit many of the physical and chemical properties characteristic of substances containing conjugated double bonds. For example, the absorption spectrum of a double bond conjugated with a cyclopropane ring is shifted toward longer wave lengths, the shift being somewhat less than that observed for conjugated double bonds and a detailed investigation of three type reactions showed that a cyclopropane ring conjugated with a carbonyl group behaved in a manner not fundamentally different from the corresponding α,β-unsaturated carbonyl compounds. Since conjugation usually has a considerable effect on electric dipole moment, we have determined the electric moments of cyclopropyl chloride, cyclopropylidene chloride and cyclopropyl cyanide for comparison with those of the corresponding cyclopentyl compounds in which conjugation was expected to be unimportant. The moments of some other cyclopentyl derivatives which have not been reported previously were also determined.