SINDO1 STUDY OF PHOTOCHEMICAL-SYNTHESIS OF AZACYCLOBUTADIENE FROM 1,3-OXAZIN-6-ONE

被引：6

作者：

NEUMANN, F ^{[1
]}

JUG, K ^{[1
]}

机构：

[1] UNIV HANNOVER,D-30167 HANNOVER,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SINDO1 calculations were performed on the photochemical reaction of 1,3-oxazin-6-one to azacyclobutadiene and carbon dioxide. The mechanism was compared with the corresponding reaction for cyclobutadiene and found to be similar. Again the first step transforms 1,3-oxazin-6-one into a bicyclic lactone via internal cyclization. Then a stepwise bond breaking mechanism on the first excited singlet state yields azacyclobutadiene and CO2, whereas a simultaneous bond breaking mechanism is not possible. In addition, a rearrangement of the bicyclic lactone on the first excited triplet surface leads to tricyclo[2.1.1.0(5.6)]-5-aza-3-oxahexan-2-one.

引用

页码：6442 / 6447

页数：6

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