RATES OF PROTON EXCHANGE AND EPIMERIZATION FOR DL- AND MESO-ALPHA-METHYLBENZYL SULFONES

被引：31

作者：

BORDWELL, FG

PHILLIPS, DD

WILLIAMS, JM

机构：

[1] Chemistry Department of Northwestern University, Evanston

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 02期

关键词：

D O I：

10.1021/ja01004a038

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ratio of the rate of deuterium exchange to the rate of epimerization for dl- and meso-a-methylbenzyl sulfones in methanol has been found to be 90:1 at 25°. This result confirms the relative insensitivity of the ke/kα ratio to substitution of Ph for R in MeCHRSO2C6H5. It is concluded that [PhCMeSO2R]- carbanions are rapidly inverting (effectively planar). © 1968, American Chemical Society. All rights reserved.

引用

页码：426 / &

共 14 条

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[8] COREY EJ, 1965, TETRAHEDRON LETT, P793
[9] EFFECT OF STRUCTURE OF CARBANION-STABILIZING SUBSTITUENTS ON STEREOCHEMICAL COURSE OF HYDROGEN-DEUTERIUM EXCHANGE REACTIONS AT SATURATED CARBON
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NIELSEN, WD
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (24) : 6415 - 6416
[10] ELECTROPHILIC SUBSTITUTION AT SATURATED CARBON .15. ASYMMETRIC CARBANIONS, ASYMMETRIC SOLVATION AND D-ORBITALS OF SULFUR
CRAM, DJ
SCOTT, DA
NIELSEN, WD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (17) : 3696 - &

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