biostudies-literatureUnknown3(1)Zhang JQFor over half a century, thousands of tons of triphenylphosphine oxide Ph<sub>3</sub>P(O) have been produced every year from the chemical industries as a useless chemical waste. Here we disclose efficient transformations of Ph<sub>3</sub>P(O) with cheap resource-abundant metallic sodium finely dispersed in paraffin oil. Ph<sub>3</sub>P(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 Ph<sub>3</sub>P(O) to be used as a precious sCommunications chemistry1https://www.ebi.ac.uk/biostudies/studies/S-EPMC9812262biostudies-literatureConversion of triphenylphosphine oxide to organophosphorus via selective cleavage of C-P, O-P, and C-H bonds with sodium.PMC9812262Huang TShinohara HHan LBZhang JQYe JFujino HfalseConversion of triphenylphosphine oxide to organophosphorus via selective cleavage of C-P, O-P, and C-H bonds with sodium.For over half a century, thousands of tons of triphenylphosphine oxide Ph<sub>3</sub>P(O) have been produced every year from the chemical industries as a useless chemical waste. Here we disclose efficient transformations of Ph<sub>3</sub>P(O) with cheap resource-abundant metallic sodium finely dispersed in paraffin oil. Ph<sub>3</sub>P(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 Ph<sub>3</sub>P(O) to be used as a precious s2020-01-01T00:00:00Z2020 Jan2026-03-27T15:36:19.635Z2025-04-05T21:40:51.638ZS-EPMC98122623670334610.1038/s42004-019-0249-6