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

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 196; no. 10; pp. 902 - 910
• Main Authors: Bondarenko, Natalia A., Tcarkova, Kseniia V., Belus', Svetlana K., Artyushin, Oleg I.
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 03.10.2021; Taylor & Francis Ltd
• Subjects: 2-phenoxyethyldiphenylphosphine oxide; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; diphenylvinylphosphine oxide; Equivalence; Nucleophiles; nucleophilic addition; PH- and NH-alkylation; Phosphine oxide; Physical Sciences; Reagents; Science & Technology; β-Functionalized ethyldiphenylphosphine oxides; SULFIDES; beta-Functionalized ethyldiphenylphosphine oxides; diphenylvinylphosphine oxide; PH- and NH-alkylation; VINYLDIPHENYLPHOSPHINE OXIDE; PHOSPHORUS-CONTAINING PODANDS; ENANTIOSELECTIVE TRANSFER HYDROGENATION; RESPECT; 2-phenoxyethyldiphenylphosphine oxide; ALKALI-METAL-CATIONS; BETA-AMINOPHOSPHINE OXIDES; PHOSPHINE OXIDES; nucleophilic addition
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2021.1939346

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 Ph 2 P(O)CH 2 CH 2 OR, where R = Ph, H, or Ph 2 P(O)CH = CH 2 , in aq.KOH/DMSO and solid KOH/DMSO systems are explored in the absence of nucleophilic reagents.