Conformations of cyclopropyl vinyl ketone have been studied using
ab initio methods in an effort
to quantify the effects of conjugative overlap between the cyclopropane
ring and adjacent enone
carbonyl. With respect to the cyclopropyl carbonyl torsion,
cyclopropyl vinyl ketone exhibits a global
energy minimum in the s-cis conformer and a local energy
minimum in the s-trans conformer.
The potential energy curve obtained was used to derive torsion
parameters which were employed
in molecular mechanics studies of the conformations of the set of
bicyclo[m.1.0]alk-3-en-2-ones
having
larger ring sizes from 5- to 16-membered.