Methyl (triphenylphosphoranylidene)acetate

CAS 1099-45-2, Cat. No EN300-19609

Reagent for Wittig alkenation reactions

Methyl (triphenylphosphoranylidene)acetate, recognized as a versatile reagent, primarily serves as a reagent in Wittig alkenation reactions. This white crystalline powder maintains shelf stability and demonstrates favorable solubility in chloroform and similar solvents while displaying limited solubility in polar solvents such as water and alcohols. Except for the Witting reaction, this reagent finds uses in heterocycles synthesis. Several different ring systems can be prepared using stabilized phosphoranes, as they have both ylide and ester reactive sites. the reagent's nucleophilicity allows it to undergo alkylation with reactive electrophiles, generating phosphorus reagents amenable to subsequent transformations. The ylide can be halogenated or sulfonated to prepare more complex ylides, which can then undergo Wittig reactions to yield vinyl halides or vinyl sulfides, respectively.

Synonyms: (2-Ethoxy-2-oxoethylidene)triphenylphosphorane, (Carbethoxymethylene)triphenylphosphoran, Triphenyl-λ5-phosphanylidene)acetic acid ethyl ester, (Triphenylcarbethoxymethylene)phosphorane

Selected publication

1. (Ethoxycarbonylmethylene)Triphenylphosphorane.

Reitz A. B.; McDonnell M. E.; Nikonov G. Organic Syntheses 2012. DOI: 10.1002/047084289X.re023.pub2