Russian Chemical Bulletin

, Volume 48, Issue 11, pp 2049–2054 | Cite as

Photoaddition of water and methanol to 2,2,4,6-tetramethyl-1,2-dihydroquinoline

  • T. D. Nekipelova
  • L. N. Kurkovskaya
  • I. I. Levina
  • N. A. Klyuev
  • V. A. Kuzmin
Physical Chemistry
  • 42 Downloads

Abstract

Products of the steady-state photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline (1) in water, methanol, and water—ethanol were isolated for the first time and identified by1H and13C NMR spectroscopy, IR spectroscopy, and mass spectrometry. As a result of the photolysis, the molecule of the solvent is added to the double bond of the heterocycle with formation of 4-hydroxy- (2) or 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline (3) in water and methanol, respectively. Compounds2 and3 are converted gradually into1 in the dark. The rate of the back reaction depends on the solvent and the concentration of the product. Comparison of the products of the photolysis in methanol and hexane at 45 °C and of the azoisobutyronitrile-initiated oxidation of1 at the same temperature has shown that unlike the photolysis in hexane, aminyl radicals are not precursors of the product of the photolysis in methanol. The reaction proceedsvia an excited singlet state.

Key words

1,2-dihydroquinolines photoaddition to the double bond steady-state photolysis effect of a solvent 1H and13C NMR 

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Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • T. D. Nekipelova
    • 1
  • L. N. Kurkovskaya
    • 1
  • I. I. Levina
    • 1
  • N. A. Klyuev
    • 2
  • V. A. Kuzmin
    • 1
  1. 1.N. M. Emanuel' Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Severtsov Institute of Ecology and Evolutionrussian Academy of SciencesMoscowRussian Federation

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