EXCEPTIONAL REACTIVITY OF THE AROMATIC RING IN 8-SUBSTITUTED 1-NAPHTHOL DERIVATIVES. READY REDUCTION TO TETRALINS.

Article abstract of DOI:10.1016/S0040-4020(01)86221-9

8-Lithio-1-methoxynaphthalene is acylated and alkylated to give 8-CO2H, COCH3 and Me2C(OH) derivatives in only poor yields.Methyl lithium does not add to the 8-acetyl compound, converting it instead to the lithium enolate.Compounds with secondary or tertiary alkyl peri-substituents undergo rapid protodealkylation, and are readily reduced to tetralins by H2/Pd at atmospheric pressure.