Synthesis of fluorous trialkyl phosphines with the complete exclusion of PH3

Tetrahedron Letters

Volumn 46, Issue 49, 2005, Pages 8605-8608

  Vlád, Gábor ^a   Richter, Frank U ^b   Horváth, István T ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b Formerly Baver Material Science AG   (Germany)

Author keywords

Fluorous; Phosphine oxides; Phosphines; Phosphonium salts; Radical addition

Indexed keywords

PHOSPHINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 27644460573     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.166     Document Type: Article

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23. 2 (7.30 mmol), and AIBN (100 mg, 8 mol %) under nitrogen. The bottle was closed and the biphasic mixture was stirred at 78-80 °C for 2 h. AIBN (100 mg) was added after every 2 h (four times), and finally the homogeneous mixture was stirred for 7 h. The resulting slightly yellow oil/solid was placed under vacuum (0.05 mbar) at 80 °C in order to remove the excess fluorous olefin and the tetramethyl-succinonitrile giving the corresponding bis(perfluoroalkyl-alkyl) phenylphosphine. This phosphine could be recrystallized from isooctane at low temperature, if needed.
24. 2 was added to the yellowish solid, the mixture was finely powdered in a mortar, and filtered through a Büchner funnel. Washing with 2 × 10 mL of FC-72 and drying in vacuo resulted in the corresponding phosphonium salt as a white or slightly yellow powder.
25. G.W. Fenton, and C.K. Ingold J. Chem. Soc. 1929 2342 2357
26. 3PO was isolated by filtration of the biphasic mixture through a Büchner funnel and drying in vacuum.
27. 2-free FC-72, filtered under nitrogen, and evaporated again. The resulting solid or oil was dissolved in 10 mL of FC-72, filtered, and evaporated in vacuo (0.05 mbar) to give the corresponding phosphine.