THEORETICAL-STUDY OF THE GAS-PHASE THERMAL-ISOMERIZATION OF ISOXAZOLES .1. ISOXAZOLE

被引：9

作者：

DAVICO, GE ^{[1
]}

PEREZ, JD ^{[1
]}

机构：

[1] NATL UNIV CORDOBA,FAC CIENCIAS QUIM,DEPT QUIM ORGAN,INST INVEST FISICOQUIM CORDOBA,CC 61,SUC 16,RA-5016 CORDOBA,ARGENTINA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1990年 / 3卷 / 09期

关键词：

D O I：

10.1002/poc.610030910

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An MNDO study was made of the gas‐phase thermal isomerization of isoxazole to explore theoretically the proposed reaction mechanism. The results showed that isoxazole isomerizes through an azirine, as an intermediate, to oxazole via a nitrile ylide or to ketenimine, with similar activation energies, and that the first step is rate limiting, in agreement with the experimental results. These results also show that isomerization to a nitrile is possible, but in this case the energy barrier is grater than the corresponding isomerization to oxazole. The MNDO study also supports a concerted process for the rate‐limiting step, as reported earlier on the basis of experimental studies. Copyright © 1990 John Wiley & Sons Ltd.

引用

页码：611 / 619

页数：9

共 26 条

[1] CRYSTAL STRUCTURE OF 2,2'-P-PHENYLENEBIS-(5-PHENYLOXAXOLE)- POPOP [J].