Studies on organophosphorus compounds XXI. the dimer of p-methoxyphenylthionophosphine sulfide as thiation reagent. a new route to thiocarboxamides†

Studies on organophosphorus compounds XXI. the dimer of p-methoxyphenylthionophosphine sulfide as thiation reagent. a new route to thiocarboxamides†
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对有机磷化合物 XXI 的研究,对甲氧基苯硫基膦硫化物的二聚体作为硫代甲酰胺的新途径。

DOI:
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发表时间:
2010
期刊:
影响因子:
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通讯作者:
S. Lawesson
S. Lawesson
中科院分区:
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文献类型:
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作者:
S. Scheibye;B. Pedersen;S. Lawesson

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通过在80-100 °C的温度范围内使用HMPA作为溶剂与代表性系列的脂肪族和芳香族伯、仲和叔甲酰胺进行反应,研究了对甲氧基苯基硫代膦硫化物的二聚体1的硫代化性质。水杨酰苯胺在HMPA中与1反应,生成水杨酰硫代苯胺和一种新型的磷杂环化合物3,其结构经NMR和X-射线分析确定。将一系列硫代酰胺碳的13 C NMR数据制成表格。
The thiation properties of the dimer of p-methoxyphenylthionophosphine sulfide, 1, has been investigated by performing reactions with a representative series of aliphatic and aromatic primary, secondary, and tertiary carboxamides in the temperature range 80-100 °C using HMPA as solvent. This new method seems to be superior to all others as in most cases quantitative yields are found. Salicylanilide, when reacted with 1, in HMPA, yields salicylthioanilide and a new type of phosphorus heterocycle, 3, whose structure has been determined by NMR-and X-ray analyses. 13C NMR data are tabulated for a series of thioamide carbons.