Journal of the American Chemical Society

Rates and equilibria of the reaction of 2, 4, 6-triphenylthiopyrylium ion with piperidine and morpholine in dimethyl sulfoxide. An unusual proton transfer to a nitrogen …

G Doddi, G Ercolani

Index: Doddi, Giancarlo; Ercolani, Gianfranco Journal of the American Chemical Society, 1984 , vol. 106, # 23 p. 7082 - 7087

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Citation Number: 6

Abstract

Abstract: The complete set of kinetic and equilibrium constants of the reaction of 2, 4, 6- triphenylthiopyrylium ion (1) with piperidine and morpholine has been obtained in Me2S0 at 25 OC. The reaction involves the formation of both the corresponding 2H-and 4H-thiopyrans, which equilibrate to form only the more stable 2 H adduct. The kinetic data are consistent with a two-step process wherein the proton transfer from the protonated 2H-and 4H- ...