1,3-DIPOLAR CYCLOADDITION ON HETEROCYCLES .25. REGIOSELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO 3,3-METHYLENE-5,5-DIMETHYL-2-PYRROLIDINONE

被引：20

作者：

ORAVEC, P

FISERA, L

ERTL, P

VEGH, D

机构：

[1] SLOVAK UNIV TECHNOL BRATISLAVA, DEPT ORGAN CHEM, CS-81237 BRATISLAVA, CZECHOSLOVAKIA

[2] COMENIUS UNIV, INST CHEM, CS-84215 BRATISLAVA, CZECHOSLOVAKIA

来源：

MONATSHEFTE FUR CHEMIE | 1991年 / 122卷 / 10期

关键词：

1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES; REGIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; AM-1; CALCULATIONS;

D O I：

10.1007/BF00815920

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nitrile oxides add regioselectively to the carbon-carbon double bond of 3,3-methylene-5,5-dimethyl-2-pyrrolidinone (1), giving exclusively spiro-isoxazolines: 3-aryl-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro[4,4]non-2-enes 3 a-1. The regiochemistry of the 1,3-dipolar cycloaddition to 1 seems to be controlled by the steric effect of the methyl groups at the ring junction and by frontier orbital interactions.

引用

页码：821 / 828

页数：8

共 25 条

[1]

BABU TVR, 1986, J ORG CHEM, V51, P5488

[2] MECHANISTIC IMPACT OF OXIME FORMATION ACCOMPANYING 1,3-DIPOLAR CYCLO-ADDITIONS OF NITRILE OXIDES [J].