63023-79-0Relevant articles and documents
EVIDENCE FOR A CHARGE-TRANSFER MECHANISM IN THE PHOTO-OXYGENATION OF AN ENAMINE
Martin, Ned H.,Jefford, Charles W.
, p. 3949 - 3952 (1981)
Evidence for a charge-transfer mechanism in the photo-oxygenation of the enamine form of 1-benzyl-3,4-dihydroisoquinolines is presented.Substituent effects, normalized to constant enamine concentration, fit best a mechanism involving the formation of a ra
Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: Selective synthesis of 3,4-dihydroisoquinolines and isoquinolines
Silveira, Claudio C.,Bernardi, Carmem R.,Braga, Antonio L.,Kaufman, Teodoro S.
, p. 907 - 910 (2007/10/03)
In a solvent-free system, the microwave irradiation of mixtures of N-sulfonyl tetrahydroisoquinolines and 37% potassium fluoride supported on alumina selectively furnished 3,4-dihydroisoquinolines or isoquinolines, depending upon the reaction time.
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.