A mechanistic study of the reactions of formaldehyde with aniline in the presence of sulfite

JH Atherton, KH Brown, MR Crampton

Index: Atherton, John H.; Brown, Kathryn H.; Crampton, Michael R. Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 5 p. 941 - 946

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Citation Number: 2

Abstract

1H NMR results are reported for the reactions of hydroxymethanesulfonate, 1, with aniline and its derivatives to produce anilinomethanesulfonates, 3. The mechanism of the reaction involves dissociation of 1 to produce formaldehyde, as a steady state intermediate, which reacts with aniline to give a carbinolamine; subsequent dehydration and reaction with sulfite produces the product. The kinetics of individual steps have been investigated. The release ...