The Reaction of Cyclooctatetraene Oxide with Grignard Reagents

Abstract

Abstract The reaction of cyclooctatetraene oxide with ethylmagnesium bromide, phenylmagnesium bromide and t-butylmagnesium bromide was found to yield 2, 4, 6-cycloheptatrienyl-1-ethyl-, phenyl- and t-butylcarbinol respectively. The treatment of cyclooctatetraene oxide with a catalytic amount of magnesium bromide in ether afforded phenyl acetaldehyde in a 76% yield. The dehydration of the carbinols with a catalytic amount of p-toluenesulfonic acid resulted in their further rearrangement to trans-β-substituted styrenes.