Spontaneous free radical spin adduct formation and 1,3-dipolar molecular addition in reactions of cyanohalocarbons and C-phenyl N-tert-butyl nitrone (PBN)

被引：26

作者：

Sang, H ^{[1
]}

Janzen, EG ^{[1
]}

Poyer, JL ^{[1
]}

机构：

[1] OKLAHOMA MED RES FDN,NATL BIOMED CTR SPIN TRAPPING & FREE RAD,FREE RAD BIOL & AGING RES PROGRAM,OKLAHOMA CITY,OK 73104

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1996年 / 06期

关键词：

D O I：

10.1039/p29960001183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, the spin trap C-phenyl N-tert-butyl nitrone double dagger (PEN) is reported to react with cyanohalocarbons (CCl3CN, CHCl2CN, CHBr2CN and CH2BrCN) in a molecular reaction. Some 1:1 molecular adducts are produced in these reactions at room temperature in hexane via 1,3-dipolar cycloaddition. These addition compounds have been studied by GC-MS and MS-MS spectrometry. At the same time, various free radicals;are formed spontaneously from these systems; These radicals are detected by EPR spin trapping techniques and assigned as follows: carbon-centred radical ((CH2CN)-C-. and (CHBrCN)-C-.) spin adducts, nitrogen-centred radical (N-.=C-CCl2, N-.=C=CHCl and N-.=C=CHBr) spin adducts, oxygen-centred radical spin adducts and benzoyl-tert-butylaminoxyl.

引用

页码：1183 / 1189

页数：7

共 22 条

[11] THE APPLICATION OF GAS-CHROMATOGRAPHIC MASS-SPECTROMETRIC TECHNIQUES TO SPIN TRAPPING - CONVERSION OF ALPHA-PHENYL N-TERT-BUTYL NITRONE (PBN) SPIN ADDUCTS TO STABLE TRIMETHYLSILYLATED DERIVATIVES [J].