A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: Anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene

Abstract

The Birch reduction of 10b,10c-dimethyl-10b,10c-dihydropyrene 1 and anthracene could be predicted on the basis of their reduction potentials and achieved readily with aqueous titanium trichloride in near quantitative yields. Controlled reduction of a nitro group could be achieved under these conditions with the aromatic hydrocarbon remaining intact. The anion derived from the hexane obtained from reduction of 1 provided synthetic routes to derivatives of 1 inaccessible from direct substitution reactions of 1. Oxidative dimerization of the anion led to the formation of a series of interesting products. © 2003 Elsevier Science Ltd. All rights reserved.