Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates

被引：13
|
作者：
El-Gazzar, ARBA
Scholten, K
Guo, YP
Weissenbach, K
Hitzler, MG
Roth, G
Fischer, H
Jochims, JC
机构：
[1] Univ Konstanz, Fak Chem, D-78434 Constance, Germany
[2] Natl Res Ctr, Cairo, Egypt
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 14期
关键词：
D O I：
10.1039/a902505g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Isothiocyanates react as S-nucleophiles with 1-aza-2-azoniaallene salts 1 to give different types of 1,3,4-thiadiazolium salts (9, 11, 12) and 1,2,4-triazolium salts (10). Which product is formed, depends on the one hand on the ability of a substituent of the heteroallene salt 1 to undergo a [1,2] shift as a positively charged migrant (generalized Wagner-Meerwein rearrangement) or to act as a cationic leaving group, and on the other hand on Dimroth rearrangement of the initially formed thiadiazolium salt 8 to triazolium salts. The structures of the thiadiazolium salt 9c and the triazolium salt 10d were confirmed by X-ray structural analyses.
引用
收藏
页码：1999 / 2010
页数：12
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