Tetrahedron

A study of the tautomerism of 2-and 4-ethoxycarbonylthiolan-3-ones implicating stereochemical effects of ring-substitution

F Duus

Index: DUUS, F. Tetrahedron, 1981 , vol. 37, # 15 p. 2633 - 2640

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Citation Number: 15

Abstract

A series of 2-and 4-ethoxycarbonylthiolan-3-ones have been synthesized and studied by 1H NMR and IR spectroscopy. Under conditions of tautomeric equilibrium in tetrachloromethane solution the 4-ethoxycarbonylthiolan-3-ones are generally more enolized (40–74%) than the 2-ethoxycarbonylthiolan-3-ones (6–34%), and both series of compounds generally are less enolized than six-membered ring analogues. The extent of enolization of the title ...

~34%

~0%

~59%

~31%

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