Abstract
Photolysis of 2,2,4,6-tetramethyl- (1) and 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline (2) in methanolic alkali yields only 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline in the former case and a mixture of 4-methoxy- and 4-hydroxy-1,2,2,4,6-pentamethyl-1,2,3,4-tetrahydroquinoline in the latter case. This result was rationalized by the existence of two resonance structures of an intermediate cation, viz., carbocationic and ortho-quinomethaneiminium species. The cation from 1 reacts with an alkali in the ortho-quinomethaneiminium form, and the cation generated from 2 reacts in the carbocationic form.
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Nekipelova, T.D., Kurkovskaya, L.N. & Levina, I.I. Dual reactivity of an intermediate cation formed in the photolysis of dihydroquinolines in methanol. Russian Chemical Bulletin 51, 2055–2058 (2002). https://doi.org/10.1023/A:1021659809874
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DOI: https://doi.org/10.1023/A:1021659809874