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Synthesis and Photo‐oxygenation of Some Substituted 1‐Benzyl‐3,4‐dihydroisoquinolines. Mechanism of Enamine Photo‐oxygenation
Author(s) -
Martin Ned H.,
Jefford Charles W.
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650314
Subject(s) - chemistry , enamine , oxygenation , tautomer , photochemistry , limiting , oxygen , combinatorial chemistry , organic chemistry , catalysis , mechanical engineering , ecology , engineering , biology
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.