REACTIVE INTERMEDIATES .I. SYNTHESIS AND OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE
REACTIVE INTERMEDIATES .I. SYNTHESIS AND OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE
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DOI：
10.1039/j39690000742
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发表时间：
1969-01-01
期刊：
影响因子：
--
通讯作者：
REES, CW
中科院分区：
文献类型：
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作者：
CAMPBELL, CD;REES, CW
以邻硝基苯胺(54%)为原料，通过苯并三唑与羟胺-O-磺酸的胺化反应，经四步反应合成了1-氨基苯并三氮唑。在后一反应中还生成了2-氨基苯并三氮唑。在非常温和的条件下，用四醋酸铅氧化1-氨基苯并三氮唑，几乎定量地得到苯并炔，在没有捕捉剂的情况下，二聚体以异常高的产率生成联苯。还生成了微量的三苯基和2-乙酰氧基联苯。2-氨基苯并三氮唑与四醋酸铅或二醋酸碘苯氧化，高产率地得到顺式，顺式-异氰酸酯。
1-Aminobenzotriazole is prepared in four steps from o-nitroaniline (54%) and, directly, by the amination of benzotriazole with hydroxylamine-O-sulphonic acid. 2-Aminobenzotriazole is also formed in the latter reaction. Oxidation of 1-aminobenzotriazole with lead tetra-acetate, under very mild conditions, gives benzyne almost quantitatively which, in the absence of trapping agents, dimerises to biphenylene in unusually high yield. Trace amounts of triphenylene and 2-acetoxybiphenylene are also formed. Oxidation of 2-aminobenzotriazole with lead tetra-acetate or with iodobenzene diacetate gives cis,cis-mucononitrile in high yield.