Synthesis of 10-Spirocyclopropyl-9-methylene-9,10-dihydroanthracene by a Novel Alcohol Dehydration Procedure

Abstract Though there exists a wide variety of methods for the preparation of olefins from alcohols, there are few which allow this conversion under basic conditions at moderate temperatures. We required such a reaction for the preparation of 10-spirocyclopropyl-9-methylene-9, 10-dihydroanthracene (1) since the compound was expected to undergo facile thermal and acid catalyzed rearrangement (Scheme I) from experience with related compounds2,3,4 and by analogy to the chemistry of other ‘blocked’ aromatic systems. 5