The Chemistry of Derivatives of 2-Benzaltetralone. I. A Novel Rearrangement Leading to 2-Substituted-l-naphthols

In the presence of an excess of a primary or secondary amine (cyclohexylamine, piperidine, morpholine, N-methylcyclohexylamine), 2-bromo-2-(α-bromobenzyl)-l-tetralone (I) reacted to give good yields of the corresponding 2-(α-aminobenzyl)-l-naphtbols (II). The structures of the naphthols were established by synthesis via Mannich condensation. In a similar manner, 2-bromo-2-benzyl-l-tetralone was dehydrobrominated and rearranged in the cold to yield 2-benzyl-l-naphthol. These results are discussed.