NOVEL DIMROTH REARRANGEMENTS OF THE BENZOTRIAZOLE SYSTEM - 4-AMINO-1-(ARYLSULFONYL)BENZOTRIAZOLES TO 4-[(ARYLSULFONYL)AMINO]BENZOTRIAZOLES

被引：41

作者：

KATRITZKY, AR ^{[1
]}

JI, FB ^{[1
]}

FAN, WQ ^{[1
]}

GALLOS, JK ^{[1
]}

GREENHILL, JV ^{[1
]}

KING, RW ^{[1
]}

STEEL, PJ ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of mono- and diarylsulfonyl-substituted 4-aminobenzotriazoles were prepared. Thermal rearrangements of 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles were observed and confirmed by separation of the rearrangement products. Their structures were characterized by spectral methods and by X-ray crystallography. The rearrangement rates were studied by variable-temperature NMR experiments. Crossover experiments support an intramolecular mechanism involving a heterolytic benzotriazole ring cleavage to form a diazo intermediate followed by recyclization to the 4-amino group.

引用

页码：190 / 195

页数：6

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