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Conversion of triphenylphosphine oxide to organophosphorus via selective cleavage of C-P, O-P, and C-H bonds with sodium
Communications Chemistry ( IF 5.9 ) Pub Date : 2020-01-03 , DOI: 10.1038/s42004-019-0249-6
Jian-Qiu Zhang 1, 2 , Jingjing Ye 1, 2 , Tianzeng Huang 1, 2 , Hiroyuki Shinohara 3 , Hiroyoshi Fujino 3 , Li-Biao Han 1, 2
Affiliation  

For over half a century, thousands of tons of triphenylphosphine oxide Ph3P(O) have been produced every year from the chemical industries as a useless chemical waste. Here we disclose efficient transformations of Ph3P(O) with cheap resource-abundant metallic sodium finely dispersed in paraffin oil. Ph3P(O) can be easily and selectively transformed to three reactive organophosphorus intermediates—sodium diphenylphosphinite, sodium 5H-benzo[b]phosphindol-5-olate and sodium benzo[b]phosphindol-5-ide—that efficiently give the corresponding functional organophosphorus compounds in good yields. These functional organophosphorus compounds are difficult to prepare but highly industrially useful compounds. This may allow Ph3P(O) to be used as a precious starting material for highly valuable phosphorus compounds.



中文翻译:

通过选择性裂解 CP、OP 和 CH 键与钠将三苯基氧化膦转化为有机磷

半个多世纪以来,化学工业每年都会产生数千吨三苯基氧化膦 Ph 3 P(O) 作为无用的化学废料。在这里,我们公开了 Ph 3 P(O) 与廉价的资源丰富的金属钠精细分散在石蜡油中的有效转化。Ph 3 P(O) 可以很容易地选择性地转化为三种活性有机磷中间体——二苯基亚膦酸钠、5H-苯并[b]膦醇-5-醇酸钠和苯并[b]膦醇-5-胺钠——有效地得到相应的收率高的功能性有机磷化合物。这些功能性有机磷化合物难以制备但在工业上非常有用的化合物。这可能允许 Ph 3P(O) 可用作高价值磷化合物的珍贵原料。

更新日期:2020-01-03
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