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33S NMR spectroscopy: Substituent γ-effect. Halogen derivatives of tetrahydrothiophene 1,1-dioxide

✍ Scribed by A. B. Rozhenko; V. M. Bzhezovsky; V. V. Polovinko; A. G. Makarenko


Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
327 KB
Volume
33
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

A series of halogen‐substituted tetrahydrothiophene 1,1‐dioxides (sulpholanes) were investigated by ^13^C, ^17^O and ^33^S NMR spectroscopy. It was shown that successive replacement of hydrogen atoms in positions 3 and 4 of the sulpholane ring led to an increase in ^33^S nuclei shielding. The ^33^S NMR chemical shift range exceeded 39 ppm. The variation of the ^33^S nuclei shielding with increasing number of chlorine or bromine atoms was caused by an electrostatic through‐space effect of the halogen atoms and the strongly polarized CHal bonds.