Structure et réactions du composé d'addition: triphénylphosphine ‐ anhydride maléique

Abstract

The structure of the adduct between maleic anhydride and triphenylphosphine has been determined by direct synthesis and spectral analysis. It is analogous to a phosphine methylene derivative (WITTIG reagent) stabilized by an u‐carbonyl group. With aldehydes, it gave none or very poor yields of the expected olefins; water (or alcohols) caused the anhydride ring to open, instead of forming triphenylphosphine oxide plus the corresponding hydrocarbon.

On the reactivity of triphenylphosphoranylidenesuccinic anhydride with nitrogen nucleophiles: a new synthetic route to nitrogen-containing phosphonium salts

“…2, Scheme 1), while reacting at C-5 with diethylamine to produce 4 (eq. 3) 8 . To provide insight into the reactivity of TPPSA we began our study varying the steric hindrance and the electronic nature of the nitrogen-nucleophiles.…”

“…1, Scheme 1), methanol, and ethanol (eq. 2) were reported as examples of behavior towards oxygen nucleophiles 8 . There is only one example of reaction of TPPSA with a nitrogen nucleophile, diethylamine (eq.…”

“…There is only one example of reaction of TPPSA with a nitrogen nucleophile, diethylamine (eq. 3), wherein the phosphinoxide 4 was reportedly obtained in low yield 8 . In view of the limited data available concerning the reactivity of TPPSA, a study of the chemical behavior of 1 toward a broad spectrum of nitrogen nucleophiles was considered to be appropriate.…”

A Useful Synthesis of Alkylidenesuccinic Acids by Wittig Reaction in Aqueous Media

“…Firstly, Wittig reagent of the stable ylide 2, (14) which is used as starting material, was prepared efficiently by the way of two step reaction in good yield from maleic anhydride and triphenylphosphine as shown in Scheme 1.…”

Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′ -tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene–oxolane-2,5,5′-trione

“…Herewith, the data for the reactivity of triphenylphosphine in this reaction remain controversial. Some authors propose the formation of betaine compounds with C-O-P + fragment (Schönberg & Ismail, 1940); others assign the structure of the reaction product as phosphorus ylides (Hudson & Chopard, 1963;Osuch et al, 1964). Ac-*Corresponding author, e-mail: abogdanov@inbox.ru Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 6/8/15 8:42 AM cordingly, the study of the interaction of maleic anhydride derivatives with trivalent phosphorus nucleophiles remains of interest and topical.…”