75397-66-9Relevant academic research and scientific papers
Synthesis and Photo-oxygenation of Some Substituted 1-Benzyl-3,4-dihydroisoquinolines. Mechanism of Enamine Photo-oxygenation
Martin, Ned H.,Jefford, Charles W.
, p. 762 - 774 (2007/10/02)
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.
REGIOPSPECIFIC OXIDATION OF SUBSTITUTED 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING SINGLET OXYGEN
Martin, Ned H.,Champion, Sidney L.,Belt, Phillip B.
, p. 2613 - 2616 (2007/10/02)
Singlet oxygen regiospecifically oxidizes 1-benzyl-3,4-dihydroisoquinoline to 1-benzoyl-3,4-dihydroisoquinoline.Mechanistic studies do not distinguish between a dioxetane or the alternative zwitterionic peroxide intermediate.
