54599-18-7

Upstream product

• 98-86-2 acetophenone 
• 13716-45-5 diethyl trimethylsilyl phosphite 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 74-88-4 methyl iodide 
• 100-52-7 benzaldehyde 

Downstream Products

• 34881-11-3 diethyl 1-hydroxy-1-phenylethylphosphonate 
• 85166-79-6 Methanesulfonic acid 1-(diethoxy-phosphoryl)-1-phenyl-ethyl ester 
• 85166-80-9 Methanesulfinic acid 1-(diethoxy-phosphoryl)-1-phenyl-ethyl ester 
• 85166-85-4 Acetic acid 1-(diethoxy-phosphoryl)-1-phenyl-ethyl ester 
• 63573-19-3 (1-Ethoxy-1-phenyl-ethyl)-phosphonic acid diethyl ester 
• 85166-86-5 (1-Methoxy-1-phenyl-ethyl)-phosphonic acid diethyl ester 
• 25944-64-3 diethyl (1-phenylethenyl)phosphonate 

Relevant academic research and scientific papers

Mesylate Derivatives of α-Hydroxy Phosphonates. Formation of Carbocations Adjacent to the Diethyl Phosphonate Group

Mesylates 3-6 have been prepared and reacted in a variety of solvents.Product, rate, and solvent effect studies implicate carbocationic intermediates in these solvolyses despite the electron-withdrawing PO(OEt)2 group.Mesylate 3 gave exclusive substitution products.Optically active 3 gave racemic products on trifluoroacetolysis. α-Deuterium isotope effects were also in line with a cationic intermediate.Mesylate 4 gave some elimination product, 27, along with the substitution product 28, also via a cationic intermediate.Mesylates 5 and 6 gave exclusive elimination products.A β-deuterium isotope effect study gave a kH6/kD6 value of 2.8.This isotope effect, along with a small m value (0.45), suggested the intermediacy of a reversibly formed ion pair which subsequently loses a proton.This mechanism represents the merging of the classical E1 mechanism and the E2C(+) mechanism, the latter representing the cationic counterpart of the E1cb mechanism.Analysis of the solvolysis rates of 3 and 4 led to the conclusion that cationic intermediates are formed quite easily.Reasons are suggested for this unexpectedly facile generation of cations adjacent to the potent electron-withdrawing PO(OEt)2 substituent.

Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)-alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives

Carbonyl addition compounds of diethyl trimethylsilyl phosphite (DTMSP) with aldehydes were converted, by treatment with lithium diisopropylamide (LDA) followed by the successive alkylation and alkaline hydrolysis, to carbonyl derivatives involving aldehydes, unsymmetrical ketones, β,γ-unsaturated ketones, and carboxylic acids. β-Substituted carboxylic esters and γ-substituted lactones were prepared by use of the carbonyl addition compounds of DTMSP with α,β-unsaturated aldehydes.