Arynic Condensations of Ketone Enolates. 15. New Synthetic Applications of the Condensation of α,β-Unsaturated Ketone Enolates on Benzyne

Article abstract of DOI:10.1021/jo01290a007

Arynic condensations of both cyclic and acyclic α,β-unsaturated ketone enolates are studied.First, condensation of substituted cyclohexenone enolates with benzyne leads to a new class of cyclobutanic alcohols 6.Ring opening of 6 under basic conditions is described as a good means of synthesizing benzocyclooctadienones 10 and 19, and, in appropriate cases, benzocyclooctenediones of type 12.Thermal dehydration of 6 affords 1,3-disubstituted naphthalenes in good yields.Second, condensations of a few acyclic α,β-unsaturated ketone enolates with benzyne are shown to be of synthetic usefulness; depending on the substituents on both sides of the carbonyl group, these condensations may lead either to substituted naphthalenes or to phenyl ketones or tetralones.