The synthesis of a series of substituted 1‐benzyl‐3,4‐dihydroisoquinolines by Bischler‐Napieralski cyclization is described. Competitive methylene blue sensitized photo‐oxygenation experiments allowed the determination of relative rates of photo‐oxygenation of 1‐benzyl‐3,4‐dihydroisoquinolines, Substituents were shown to affect both the equilibrium concentration of the tautomeric enamine and the overall photo‐oxygenation rate. After correcting for differences in enamine concentration, the relative rate data provided a diagnostic probe of the reaction mechanism, which involves transfer of charge in the rate‐limiting step.
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Martin et al. (1982) studied this question.
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