The Journal of Organic Chemistry

Nature of the reaction of thiamin in the presence of low concentrations of sulfite ion. Competitive trapping

JA Zoltewicz, G Uray

Index: Zoltewicz, John A.; Uray, Georg Journal of Organic Chemistry, 1981 , vol. 46, # 11 p. 2398 - 2400

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Citation Number: 10

Abstract

Nucleophilic substitution of thiamin (11, vitamin B1, by sulfite ion gives pyrimidinium sulfonate 2 and the corresponding free thiazole.'Although this reaction was first reported in 1935 it was not until 1977 that a mechanism was advanced: one sulfite ion adds to the pyrimidinium ring, made electrophilic by protonation, to give intermediate 3. A second sulfite ion, the one appearing in the observed product, then reacts either with 3 or with another ...