Reactions of substituted 1-oxaspiro- and 1-azaspiro-[3.5]nona-5,8-diene-2,7-diones with nucleophiles

Abstract

The reactions of substituted 3,3-diphenyl-1-oxaspiro[3.5]nona-5,8-diene-2,7-diones with nucleophiles such as potassium cyanide, methylmagnesium iodide, and methyl-lithium produce (p-hydroxyphenyl)diphenylmethyl derivatives in good yield. The reactions can be explained in terms of formation of a p-quinone diphenylmethide as intermediate followed by 1,6-addition of the nucleophiles. The reactions of 3,3-dimethyl-1-oxaspiro[3.5]nona-5,8-diene-2,7-diones, substituted 1-azaspiro[3.5]nona-5,8-diene-2,7-diones, and other spiro-β-lactams With methyl- and p-tolyl-lithium were also examined.