2-Alkenyldiphenylphosphine Oxides and PO-Ylids Derived Thereof in trans Selective Horner-Wittig Olefination Reactions

Synlett

Volumn 1996, Issue 12, 1996, Pages 1195-1196

  Liu, Rong Qiang ^a   Schlosser, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005793313     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5700     Document Type: Article

References (40)

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37. Standard conditions : At -75 °C, butyllithium (25 mmol) in hexane (15 mL) is added to the phosphine oxide (25 mmol) in tetrahydrofuran (85 mL). After 30 min of stirring, the aldehyde (25 mmol) is added dropwise in the course of 15 min, still at -75 °C The mixture is kept for 2 h at 25 °C before being adsorbed on silica gel (25 mL). Elution with hexane from a column filled with more silica gel (75 mL) and evaporation of the solvent gave a colorless oil, the stereoisomeric composition of which was analyzed by gas chromatography (30 m, dimethylpolysiloxane rubber DB-1, 60-180 °C; 30 m, DB-FFAP [polyethylene glycol + nitroterephthalic acid], 100-200 °C) The diene was isolated by distillation under reduced pressure.
38. 24 (prepared from diethyl phosphite with 3 molar equivalents of phenylmagnesium bromide). - Further experimental details concerning the preparation of the 2-alkenylphosphine oxides and the characterization of the olefination products will be published in a Feature Article to appear 1997 in Synthesis.
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