7751-69-1Relevant articles and documents
The synthesis of benzylphosphine oxidesvia vicarious nucleophilic substitution and alkenes via VNS-Horner-Wittig reactions
Lawrence, Nicholas J.,Liddle, John,Jackson, David
, p. 2260 - 2267 (2007/10/03)
A range of substituted nitrobenzenes react with the anion of (chloromethyl)diphenylphosphinoyl oxide to give the substituted nitrobenzyldiphenylphosphine oxide by vicarious nucleophilic substitution. The novel stereoselective synthesis of E-stilbenes via a one-pot vicarious nucleophilic substitution-Horner-Wittig reaction is described.
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.
