2-Phenoxyethyldiphenylphosphine oxide as an equivalent of diphenylvinylphosphine oxide in nucleophilic additions

Abstract

A facile method for the synthesis of β-functionalized ethyldiphenylphosphine oxides is developed based on readily available 2-phenoxyethyldiphenylphosphine oxide used as an equivalent of diphenylvinylphosphine oxide in the reactions of addition of different PH- and NH-nucleophiles in DMSO in the presence of KOH. The transformations of labile phosphine oxides of a general formula Ph₂P(O)CH₂CH₂OR, where R = Ph, H, or Ph₂P(O)CH = CH₂, in aq.KOH/DMSO and solid KOH/DMSO systems are explored in the absence of nucleophilic reagents.

Graphical Abstract

Keywords:

• β-Functionalized ethyldiphenylphosphine oxides
• 2-phenoxyethyldiphenylphosphine oxide
• diphenylvinylphosphine oxide
• nucleophilic addition
• PH- and NH-alkylation

Conflict of interests

The authors declare no conflict of interests.

Notes

1 The organic layer was washed until precipitation of Ph₂P(O)OH during acidification of the washings.

2 Two conformers (1:1).

3 To remove the DMSO residues into a trap cooled with liquid nitrogen.

Additional information

Funding

This work was performed with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of the Center for Collective Use of NRS «Kurchatov Institute» - IREA, NRS «Kurchatov Institute» and the Center for Molecular Composition Studies of INEOS RAS.