SILICON-MODIFIED BIRCH REDUCTION AND REDUCTIVE ALKYLATION OF POLYNUCLEAR AROMATICS

Article abstract of DOI:10.1016/S0040-4020(01)89490-4

A trimethylsilyl substituent is used to control regiochemistry, overreduction, and prevent bond cleavage during the metal/ammonia reduction of aromatic and polynuclear aromatic compounds.The trimethylsilyl group is then removed by tetrabutylammonium fluoride and replaced by either hydrogen or primary alkyl, the latter case representing overall reductive alkylation.Results are presented for naphtalene together with its 1-methyl, 2-methyl and 2-methoxy derivatives, phenanthrene and its 9-methyl and 9-ethyl derivatives, biphenyl and triptycene.