Preparation and Reactions of Dianions from the Cresols

Article abstract of DOI:10.1021/jo00359a010

With n-BuLi/KO-t-Bu, protons are removed from the hydroxyl and methyl groups of cresols 5 to give dianions 6 in yields of 85percent (ortho), 95percent (meta), and 42percent (para).These dianions react with alkyl halides, Me3SiCl, Bu3SnCl, CO2, and oxidizing agents at carbon only and with dialkyl sulfates at both carbon and oxygen.Thus phenol derivatives bearing primary alkyl groups can be prepared from the corresponding methylphenols via dianions 6.