Conversion of triphenylphosphine oxide to organophosphorus via selective cleavage of C-P, O-P, and C-H bonds with sodium
| Autor: | Hiroyoshi Fujino, Tianzeng Huang, Hiroyuki Shinohara, Jingjing Ye, Jian-Qiu Zhang, Li-Biao Han |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Sodium Phosphorus chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Selective cleavage Waste product Metal lcsh:Chemistry chemistry.chemical_compound lcsh:QD1-999 Organophosphorous compounds visual_art Wittig reaction Materials Chemistry visual_art.visual_art_medium Environmental Chemistry Organic chemistry Triphenylphosphine oxide |
| Zdroj: | Communications Chemistry, Vol 3, Iss 1, Pp 1-9 (2020) |
| ISSN: | 2399-3669 |
| Popis: | 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. As a byproduct of organic syntheses including the Wittig, Staudinger, and Mitsunobu reactions, triphenylphosphine oxide is often not recycled. Here a transformation of the waste product with metallic sodium to three organophosphorous compounds is presented. |
| Databáze: | OpenAIRE |
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