STRUCTURES OF ADDUCTS OF N-PHENYLHYDROXYLAMINE WITH DIMETHYL ACETYLENEDICARBOXYLATE
STRUCTURES OF ADDUCTS OF N-PHENYLHYDROXYLAMINE WITH DIMETHYL ACETYLENEDICARBOXYLATE
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DOI：
10.1021/jo01065a008
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发表时间：
1961-01-01
影响因子：
3.6
通讯作者：
AGOSTA, WC
中科院分区：
文献类型：
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作者：
AGOSTA, WC
对V-苯羟胺与乙酰二甲酸二甲酯的2：2和2：1加合物分别提出了结构II和结构III。简要讨论了由苯胺、草酸二甲酯和Q-溴代乙酸二甲酯独立生成III对Hantzsch吡咯合成机理的影响。已知乙酰二甲酸二甲酯和IV-苯羟胺反应生成两种结晶加合物，一种不稳定的物质，加合物的比例为1：1，另一种稳定的化合物由两个酯分子组成。1*虽然Huntress1能够通过指数获得后者的加成物-
Structures II and III are proposed for the 2: 2 and 2: 1 adducts, respectively, ofV-phenylhydroxylamine with dimethyl acetylenedicarboxylate. Implications of the independent formation of III from aniline, dimethyl oxalacetate, and dimethyl Q-bromoxalacetate for the mechanism of the Hantzsch pyrrole synthesis are briefly discussed.Dimethyl acetylenedicarboxylate and IV-phenylhydroxylamine are known to react to produce two crystalline adducts, an unstable material in which the addends are present in the ratio 1: 1, and a stable compound consisting of two molecules of ester for each one of amine. 1* Although Huntress1 was able toobtain the latter adduct by an inde-