The Journal of Organic Chemistry

Kinetic and thermodynamic study of the reaction of 2, 4, 6-triphenylthiopyrylium ion with butylamine and cyclohexylamine in dimethyl sulfoxide

G Doddi, G Ercolani

Index: Doddi, Giancarlo; Ercolani, Gianfranco Journal of Organic Chemistry, 1984 , vol. 49, p. 1806 - 1810

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Citation Number: 6

Abstract

A kinetic and thermodynamic study of the reaction of the 2, 4, 6-triphenylthiopyrylium ion (1) with butylamine and cyclohexylamine has been performed in MezSO at 25" C. The reaction involves the initial formation of both the corresponding 2H-and 4H-thiopyrans, which equilibrate to form only the more stable 2H adduct. The kinetic data are consistent with a two- step process wherein the formation of the protonated 2H-and 4H-thiopyran intermediates ...