83199-89-7

Upstream product

• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 645-45-4 hydrocinnamic acid chloride 
• 83199-82-0 t-Butyl 5-Chloro-3-oxo-2-(triphenylphosphoranylidene)-pentanoate 
• 603-35-0 triphenylphosphine 
• 1262551-94-9 C₃₀H₃₆O₆P₂ 
• 100-52-7 benzaldehyde 
• 83207-71-0 tert-butyl 3-oxo-5-phenyl-2-(triphenylphosphoranylidene)-(E)-4-pentenoate 
• 107-59-5 tert-Butyl chloroacetate 
• 83199-83-1 tert-butyl 3-oxo-2-(triphenylphosphoranylidene)-4-pentenoate 
• 591-51-5 phenyllithium 

Downstream Products

• 16640-69-0 4-phenyl-1-(triphenylphosphoranylidene)butan-2-one 

Relevant academic research and scientific papers

A new synthesis of phosphorane ylide precursors to vicinal tricarbonyls from alkyl halides utilizing a novel phenylsulfonyl reagent

A unique approach to Aα-keto cyanophosphorane ylides, the key precursors to α-keto amide/ester units in Wasserman?s protocol, from alkyl halides using a novel phenylsulfonyl reagent was reported. The requisite new sulfonyl reagent was successfully synthesized from phenylsulfonylacetic acid and phosphorane ylide as a stable solid. Although deprotonation of sulfonyl reagent with NaH proceeded smoothly, alkylation of the resulting anion with benzyl chloride was found almost inactive. Benzyl bromide, however, furnished benzylated sulfonyl ylide in 94% yield. This benzylated sulfonyl ylide was cleanly separated by flash chromatography, and its structure was unambiguously corroborated by 1H-NMR spectrum.

A new synthesis of triphenylphosphorane ylide precursors to α-keto amide/ester and tricarbonyl units via horner-wadsworth-emmons reaction

Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford β,γ-unsaturated α-keto triphenylphorane ylides in good to excell

Charge-Directed Conjugate Addition Reactions in the Preparation of Substituted Methyl Ketones

Charge-directed conjugated addition reactions of the tert-butyl esters of α,β-unsaturated acylphosphoranes 2 have been used to prepare a variety of substituted methyl ketones.Substituted ylides 6 are prepared by alkylating ylide anions 4 generated by the addition of nucleophiles to 2 and are converted under acidic conditions to substituted (acylmethylene)phosphoranes 12 which are hydrolyzed to methyl ketones.The utility of these unsaturated acylphosphoranes as methyl vinyl ketone equivalents in conjugate addition-alkylation reactions is demonstrated in a synthesis of the racemic form of the sex pheromone of the California red scale, 14.