CONFORMATIONAL PREFERENCE OF THE SULFIMIDE FUNCTIONALITY IN CYCLIC SULFIMIDES

被引：21

作者：

CLAUS, PK ^{[1
]}

VIERHAPPER, FW ^{[1
]}

WILLER, RL ^{[1
]}

机构：

[1] UNIV N CAROLINA,WR KENAN JR LABS CHEM,CHAPEL HILL,NC 27514

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 16期

关键词：

D O I：

10.1021/jo01330a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformational equilibria of various >S?N-R derivatives (R = C6H4X, SO2Ar, COAr, COOEt, COMe) of thiane and of some oxa-and dithianes were determined by low-temperature 13C NMR spectroscopy. The conformational preference of the thiane 1-(N-aryl)imides was found to depend on the electron-withdrawing capacity of the substituents on the aromatic ring. Replacement of the aromatic ortho hydrogens by methyl or fluorine did not greatly change the equilibrium. A nearly constant difference in conformational free energy was found between 1-[N-(p-chlorophenyl)]imides and 1-oxides for the various heterocyclic ring systems investigated. © 1979, American Chemical Society. All rights reserved.

引用

页码：2863 / 2871

页数：9

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