Eliane Torreilles

L'aza-ylure N-lithie (C6H5)3PNLi, reactif d'amination

The preparation of the lithiated aza-ylide 3 has been improved and its one-pot reactivity toward alkyl and acyl halides to give amino-phosphonium salts and accordingly amines is described.

Mechanistic investigations of the formation of TTF derivatives via the phosphonate way

We studied the influence of acetic acid concentration on the deamination and dephosphonylation of the adduct resulting of the nucleophilic reaction between adequate α-metalated phosphonate and imminium salt. to enhance the yield of such reactions in order to access efficiently a lot of unsymmetrical TTF derivatives. A mechanism is proposed for the formation of TTF, including steps, i1 to i-. The potential concurrent formation of phosphonate 1 and other by-products is also discussed.

PHOSPHONIUM AZA-YLDIID AS REAGENT FOR ONE-POT SYNTHESIS OF PHOSPHINIMINES WITH FUNCTIONAL N-SUBSTITUENTS

Abstract A new procedure for the one-pot synthesis of phosphinimines with functional N-substituents using the alkylation of phosphonium aza-yldiid 1 with a-bromo esters or the direct introduction of phosphorus and sulfur groups.

Dethioacetalisation de dithiannes-1,3 par des tribromures de phosphonium

Abstract Methyltriphenylphosphonium tribromide 1 acts as an efficient mild dethioketalization reagent with high selectivity for 2-phenyl and 2-vinyl 1,3-dithiannes 2 versus 2-alkyl 1,3-dithiannes and without any secondary bromination reaction of the investigated substrates. The reaction was also successful with trimethylphenylammonium tribromide.

Phosphonium Diaza-Diylids and Aza-Yldiid as New and Efficient Reagents For Primary and Secondary Amines Synthesis

Abstract Metallated aminophosphonium ylids, diaza-diylids and azayldiid, are investigated as reagents for primary and secondary amines synthesis.

LES TRIBROMURES DE PHOSPHONIUMS. AGENTS DE BROMATION DE SUBSTRATS ORGANIQUES

Abstract The reactivities and selectivities of phosphonium tribromides 1–4 towards ketones and their ketals, in the presence of other functional group reactive towards bromide (free enolic position, activated aromatic ring or double bond), are studied and compared with the trimethyl phenyl ammonium tribromide 5. The abilities of the two kinds of tribromides are similar, with a better selectivity of phosphoniums salts toward unsaturated ketones, which is probably induced by the greater stability of the ion-pair in phosphonium salts. They act essentially by the tribromide without specific bond interactions between phosphorus and heteroatom of the substrate.

Convenient One Pot Preparation of Acylated Phosphinimines and Aminophosphonium Salts From the Versatile Triphenylphosphonium and Lithium Azayldiide Ph3P=N−Li

Starting from gaseous ammonia, through two multisteps reactions, either acylation or alkylation reactions, we have access to different N-substituted aminophosphonium salts, precursors of amines. Preparation and use of the intermediate, the triphenylphosphonium and lithium azayldiide Ph3P=N-Li 1, were realized in “one pot”.

ADDITIONS OF NUCLEOPHILES TO VINYL PHOSPHONIUM SALTS. A USEFUL WAY TO OBTAIN NEW SYNTHONS

Abstract The vinylphosphonium salts 2. obtained from allenyl compounds 1. are phosphorus synthetic equivalents of γ functionalized allylic carbocations. Nucleophilic addition reactions give polyfunctional phosphonium salts, useful starting materials for further investigations. As a function of the basicity of the nucleophile, the addition reaction is in competition with elimination of the phosphorus group in 2, leading to reformation of the allenic starting material 1.

Preparation et caracteristiques d'un nouveau sel de transfert de charge conducteur electrique : TMTTF3-DETCNQ2 ☆

Abstract A new organic conductor TMTTF 3 - DETCNQ 2 of unusual stoichiometry and structure is described and its spectral properties and electrical conductivity between 300 - 100°K studied.

Comparative evaluation of oxidising and nucleophilic properties of some α-nucleophiles

Six α-nucleophiles were evaluated at pH = 8 in an aqueous methanolic solution for their oxidising power towards tetrahydrothiophene, and the nucleophilic properties towards paraoxon. MMPP and m-CPBA are the most versatile reagents and can act as nucleophiles as well as oxidising agents.