REACTIONS OF N-CARBAZOLYL RADICAL

被引:39
作者
WATERS, WA
WHITE, JE
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1968年 / 06期
关键词
D O I
10.1039/j39680000740
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An attempt has been made to prepare and study the N-carbazolyl free radical. It can be obtained by thermolysis or photolysis of NN′- azocarbazole and is evidently a transient intermediate in the oxidation of carbazole with potassium permanganate or silver oxide. In inert solvents these reactions yield NN′-dicarbazolyl, 3,9′-dicarbazolyl, carbazole, and telomers in which carbazolyl radicals are linked together through either the 3- (=C) or the 9- (=N) positions. Thus N-carbazolyl radicals can attack the 3-positions of other carbazolyl radicals or of NN′-dicarbazolyl. They can also abstract hydrogen from the α-positions of toluene, cumene, and p-xylene; from reaction in the last solvent both bi-p-xylyl (4,4′- dimethylbibenzyl) and N-xylylcarbazole have been isolated. Products were identified by a combination of spectrographic techniques, and a number of new N-arylcarbazoles have been prepared.
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页码:740 / &
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