A novel heterocyclic atom exchange reaction with Lawesson's reagent: a one-pot synthesis of dithiomaltol

D Brayton, FE Jacobsen, SM Cohen…

Index: Brayton, Daniel; Jacobsen, Faith E.; Cohen, Seth M.; Farmer, Patrick J. Chemical Communications, 2006 , # 2 p. 206 - 208

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Citation Number: 14

Abstract

The 1 H NMR resonances of the ring protons (R 3 and R 4 ) allow the direct distinction of the various maltol-derived products due to the sequential downfield shifts that these protons undergo upon sulfur substitution. Fig. 1 shows their comparative spectra in CDCl 3 ; for maltol, two doublets appear at δ 6.45 and 7.73, for thiomaltol, the signals are at δ 7.33 and 7.59, and for dithiomaltol, the resonances are at δ 7.52 and 8.16. This downfield shift in the ring ...