Tetrahedron

Synthesis of 8-substituted 1-naphthylamine derivatives. exceptional reactivity of the substituents.

AJ Kirby, JM Percy

Index: Kirby, Anthony J.; Percy, Jonathan M. Tetrahedron, 1988 , vol. 44, # 22 p. 6903 - 6910

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Citation Number: 47

Abstract

8-Lithio-1-N, N-dimethylaminonaphthalene has been prepared, and converted in good yield to the 8-CHO, COCH3, n-Bu2B and OH derivatives. The peri-relationship confers special reactivity on both 1 and 8 substituents: the aldehyde (5) is largely ring-closed in acid, the borane (9) is inert to oxidation because of the B→ N interaction, and the 8-methoxymethyl NMe3+ derivative is formed only with difficulty, and readily demethylated.