Intramolecular general-base catalysis of Schiff-base hydrolysis by tertiary amino groups

T Okuyama, H Shibuya, T Fueno

Index: Okuyama; Shibuya; Fueno Journal of the American Chemical Society, 1982 , vol. 104, # 3 p. 730 - 736

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Citation Number: 23

Abstract

Conclusion The kinetics of the hydroxythiacycloalkane compounds 2, 4, and 5 suggest that oxidation occurs via two pathways. Both paths involve sulfurane formation and rate- determining hydroxyl participation followed by rapid decomposition of the bridged intermediate. Under ideal circumstances the bridged alkoxysulfonium salt can be precipitated from solution. This work confirms the hydroxyl group participation which was ...