The electrochemical oxidation of some 4-benzyltetrahydroisoquinolines.

Abstract

The cyclisation of N-methul-2-(2-hydroxymenthyl-4,5-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propionamide and related structures does not yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydro-3-3isoquinoline, but gives instead dibenzop [b,f] cycloheptane derivatives. Anodic oxidation of 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroiso-quinoline affords the corresponding 3,4-dihydroisoquinolonium and 4-(3,4-dimethoxybenzylidene)-6,7-dimethoxy-2-methyl-1,4-dihydroisoquinolinium salts. No intra-molecularly aryl-aryl coupled products are isolated. 2-Trifluoroacetyl-1,2,3,4-tetrahydro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)isoquinoline was synthesised and its electrochemistry investigated. This work was carried out in a period of 2 years, from 1977-1979.

Date of Award	1980
Original language	English
Awarding Institution	University of Bath