Alkylation-Reduction of Carbonyl Systems. V. The Selective Synthesis of o-Tolylphenylmethanol and o-Tolylphenylmethane by Phenylation-Reduction of Benzocyclobutenone

Abstract

For some time this laboratory has been developing the concept of tandem alkylation-reduction as a convenient method of preparing aromatic hydrocarbons by the lithium-ammonia reduction of benzyl alkoxides generated in situ by alkylation.¹ In these as well as related metal-ammonia reduction studies we have also demonstrated the mechanistic advantages and selective synthetic utility of comparing sodium benzoate² vis-à-vis ammonium chloride as quenching agents for the lithium-ammonia reduction step.^1a,b,3 Herein we wish to describe the application of these procedures to the strained aromatic carbonyl system benzocyclobutenone (1)⁴ that resulted in the selective synthesis of either o-tolylphenylmethanol (4) or o-tolylphenylmethane (5) depending on the quenching agent.