GRADUAL INVERSION AT PYRAMIDALLY-BOUND NITROGEN - ISOLATION AND EPIMERIZATION OF DIASTEREOMERIC N-METHOXY-3,3-DIMETHOXYCARBONYL-5-CYANO-1,2-OXAZOLIDINES

被引：71

作者：

MULLER, K

ESCHENMO.A

机构：

[1] Organisch-chemisches Laboratorium, Eidgenössischen Technischen Hochschule Zürich

来源：

HELVETICA CHIMICA ACTA | 1969年 / 52卷 / 07期

关键词：

D O I：

10.1002/hlca.19690520707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two crystalline diastereomeric N‐methoxy‐3, 3‐di‐methoxycarbonyl‐5‐cyano‐1, 2‐oxazolidines (II and III) have been isolated. The pyramidal arrangement at the respective nitrogen atoms does not invert at room temperature. The ARRHENIUS activation energy for the epimerization of the thermodynamically less stable isomer to the more stable one in bromoform solution is 29,2 ± 0,5 kcal/Mol (log A = 14,2 ± 0,3). Copyright © 1969 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1823 / &

共 68 条

[1]

ALLRED EL, 1967, TETRAHEDRON LETT, P525

[2] NUCLEAR MAGNETIC RESONANCE STUDIES OF RATE PROCESSES AND CONFORMATIONS .V. SYNCHRONOUS INVERSION AT 2 NITROGENS [J].