Bicyclo[2.2.2]octane-2-spirocyclohexanes, Part 5 [1] The Action of Grignard Reagents on Spirodiisophora-3′,6-dione

Abstract

Grignard reagents react with spirodiisophora-3',6-dione exclusively at its 3'-keto-function, yielding 3'-eq-alkyl(or phenyl)-3'-ax-hydroxyspirodiisophor-6-ones. Successive dehydration and m onobrom ination o f the methyl hom ologue yields products, the structural details o f which are settled by their 13C N M R spectra.