Hydrolyses of 2-(trimethylsilyl) N1-heterocycles. Involvement of zwitterions in the hydrolysis of 2-(trimethylsilyl)-N-methylimidazole, 2-(trimethylsilyl) pyridine, and 2-[( …

RS Brown, H Slebocka-Tilk, JM Buschek…

Index: Brown, R. S.; Slebocka-Tilk, H.; Buschek, J. M.; Ulan, J. G. Journal of the American Chemical Society, 1984 , vol. 106, # 20 p. 5979 - 5984

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Citation Number: 18

Abstract

Abstract: The title N-containing aromatic heterocycles (1, 2, and 4, respectively) with a trimethylsilyl substituent at the 2-position hydrolyze relatively rapidly to form trimethylsilanol and the corresponding 2-H heterocycle. In the case of 2-((trimethyl-sily1) methyl)-N- methylimidazole (4) the heterocyclic product is N, 2-dimethylimidazole. pH vs. log kobsd profiles establish that the reaction proceeds faster at high than low pH and that above the ...