Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes

M. Carmen Carreño; Marcos González-López; Alfonso Latorre; Antonio Urbano

doi:10.1055/s-2005-869857

LETTER

Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes

M. Carmen Carreño*, Marcos González-López, Alfonso Latorre, Antonio Urbano*
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain
Fax: 34(91)4973966; e-Mail: carmen.carrenno@uam.es; e-Mail: antonio.urbano@uam.es;

Abstract

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Abstract

Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes occurred preferentially at the A-ring when no substituents were present at the ortho-positions of the aryl group (up to 100% selectivity), to afford 1-aryl-7-methoxy-1,2,3,4-tetrahydronaphthalenes. Ortho-substitution of the 1-aryl moiety favored B-ring reduction (up to 85:15 selectivity) giving rise, after acidic hydrolysis of the vinyl ether intermediate, to the corresponding 8-aryl-2-tetralones.

Key words

biaryls - chemoselectivity - steric hindrance - reductions - sodium

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