T. Nekipelova, V. Shishkov, V. Kuzmin
May 1, 2002
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Journal
High Energy Chemistry
Abstract
The kinetics and mechanism of photoinduced addition of water and methanol to the double bond of 2,2,4-trimethyl-1,2-dihydroquinoline (DHQ) bearing different substituents in the 6- and 8-positions and N-methylated DHQ were studied by flash photolysis. The reaction affords corresponding Markovnikov adducts, 4-hydroxy- and 4-methoxy-1,2,3,4-tetrahydroquinolines. On the basis of time-resolved experiments and the measurement of quantum yields of the reaction in media of different acidities or basicities, a general scheme of the reaction is suggested, which involves the formation of two intermediate species. The principal rate constants, activation parameters, and their dependence on substituents were determined.