Synthesis of acyl(chloro)phosphines enabled by phosphinidene transfer.

ABSTRACT: Acyl(chloro)phosphines RC(O)P(Cl)(t-Bu) have been prepared by formal insertion of tert-butyl phosphinidene (t-Bu-P) from t-BuPA (A = C₁₄H₁₀ or anthracene) into the C-Cl bond of acyl chlorides. We show that the under-explored acyl(chloro)phosphine functional group provides an efficient method to prepare bis(acyl)phosphines, which are important precursors to compounds used industrially as radical polymerization initiators. Experimental and computational investigations into the mechanism of formation of acyl(chloro)phosphines by our synthetic method reveal a pathway in which chloride attacks a phosphonium intermediate and leads to the reductive loss of anthracene from the phosphorus center in a P(v) to P(iii) process. The synthet

SUBMITTER: Szkop KM 

PROVIDER: S-EPMC6432624 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature