18872-84-9Relevant academic research and scientific papers
Efficient synthesis of benzylphosphine oxides and E-stilbenes
Brown,Brown, Karen M.,Lawrence,Lawrence, Nicholas J.,Liddle,Liddle, John,Muhammad,Muhammad, Faiz,Jackson,Jackson, David A.
, p. 6733 - 6736 (2007/10/02)
A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.
Reactions of Carbonyl Compounds with Tervalent Phosphorus Reagents. Part 10. Monochlorophosphines and Aldehydes
De'ath, Norman J.,Miller, Allen J.,Nunn, John M.,Stewart, Denis
, p. 776 - 784 (2007/10/02)
The reaction of chlorophosphines (1) with aldehydes to give α-chloroalkylphosphine oxides (11) has been shown to involve two stable organophosphorus intermediates.Detailed study of the reaction of chlorodiphenylphosphine (1a) with benzaldehyde has revealed that the intermediates are α-chlorobenzyl α-(diphenylphosphinoyl)benzyl ether (8a) and bis- ether (12a), and that each is formed as one diastereoisomer only. 2-Chloro-2,2,3,5-tetraphenyl-1,4,2λ5-dioxaphospholan (4a) is suggested as the precursor of these phosphine oxides, and experimental evidence for the overall pathway to α-chlorobenzyldiphenylphosphine oxide (11a) is presented.Previous rationalisations of these complex reactions are shown to need reappraisal.
