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- Title
Reactions of intramolecular C-N photocyclization and photoaddition to the double bond of methoxy- and methoxycarbonyl-substituted styrylbenzoquinolines.
- Authors
Budyka, M.; Li, V.; Gavrishova, T.; Potashova, N.
- Abstract
Photochemical reactions of C-N photocyclization and ethanol photoaddition, which are side reactions relative to photoisomerization, have been studied for 3-(3-methoxystyryl)benzo[f]quinoline (3MSBQ) and 3-(4-methoxycarbonylstyryl)benzo[f]quinoline (4MCSBQ). The overall quantum yield of the side reactions is almost two orders of magnitude below that of photoisomerization. The presence of several photoproducts has been revealed by principal component analysis. By electrospray mass spectrometry and absorption and emission electron spectroscopy, it has been found that the photoproducts are 12b-azoniabenzo[c]chrysene derivatives formed via the intramolecular C-N photocyclization and adducts with ethanol, of which the former dominate for 3MSBQ and the latter are prevalent for 4MCSBQ. The relative stability of the primary photocyclization products for a series of styrylbenzoquinolines calculated by the DFT (B3LYP/6-31G*) method correlates qualitatively with experimental data on the formation of the final oxidized condensed products.
- Subjects
INTRAMOLECULAR catalysis; PHOTOCYCLIZATION; PHOTOADDITION; ETHANOL; PHOTOISOMERIZATION; MASS spectrometry; ELECTRON spectroscopy
- Publication
High Energy Chemistry, 2015, Vol 49, Issue 3, p158
- ISSN
0018-1439
- Publication type
Article
- DOI
10.1134/S0018143915030066