Phosphonium, tris methyl

The main method for obtaining these heterocycles is the interaction of amines with oxymethylphosphines. Frank and Drake (72JOC2752 77JOC4040) isolated 5-aminomethyl-l,3-diphenyl-l,3,5-diazaphosphori-nane (39) by treating tris(oxymethyl) phosphine (40) or tetrakis(oxy-methyl)phosphonium chloride (38) with aniline. The reaction with p-toluidine proceeds in a similar manner [Eq. (24)] (83IZV1379). 

The derivative 90 was obtained by condensation of the purpurin-18-A-hexylimide-17-propionic acid with aminolactose heptaacetate in the presence of benzotriazol-l-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) followed by the deacetylation procedure. The lactose-photosensitiser conjugate linked by an ethylene moiety was also prepared by following a similar approach. The purpurin-18-methyl ester 81 was converted into /V-(3-iodobenzyl)/ /evo-purpurin-18-7V-hexylimide-17-propionic ester by hydrogenation over Pd/C followed by reaction with 3-iodo-benzylamine. Afterwards, the propargyllactose heptaacetate reacted with A-(3-iodobenzyl)rMeio-purpurin-18-A-hexylimide-l 7-propionic ester in the presence of tris(dibenzylidieneacetone)dipalladium(0) (Pd2-dba3) which, after deacetylation conditions, afforded the derivative 89 (Fig. 9).68... 

Trimethylsilylimino) (trimethylsilyl) [tris(dimethylamino)phosphoranylidene] methyl phosphine (64), produced by the reaction of [(dichlorophosphanyl)methyl]tris (dimethylamino)phosphonium tetraphenylborate with sodium bis(trimethylsilyl)amide,... 

The C20 amino acid (2.V,3.S, 8.S, 9.S, 4/ , 6 )-3-amino-9-methoxy-2,6,8-tri-methyl-10-phenyldeca-4,6-dienoic acid (Adda 19) is a molecule of interest to biologists and organic chemists as a component of the hepatotoxic cyclic peptides called microcystins. Kim and Toogood used Ireland-Claisen rearrangement in their successful synthesis of Adda8 (Scheme 1.3h). The ester 20 underwent highly diastereoselective Ireland-Claisen rearrangement to provide the acid 21. Conversion of this acid to the phosphonium bromide 22 was achieved in nine... 

Benzyl trimethyl ammonium hydroxide Cetrimonium bromide Dimethyl diallyl ammonium chloride Laurtrimonium bromide Laurtrimonium chloride Methyl tributyl ammonium chloride Tetrabutyl ammonium bromide Tetrabutyl ammonium chloride Tetrabutyl ammonium fluoride Tetra-n-butyl ammonium hydrogen sulfate Tetra-n-butyl ammonium hydroxide Tetrabutyl ammonium iodide Tetrabutylphosphonium acetate, monoacetic acid Tetrabutylphosphonium bromide Tetrabutylphosphonium chloride Tetraethylammonium bromide Tetraethylammonium hydroxide Tetrakis (hydroxymethyl) phosphonium chloride Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium hydroxide Tetramethyl ammonium iodide Tetraphenyl phosphonium bromide Tetrapropyl ammonium bromide Tetrapropyl ammonium iodide Tributylamine Tributyl phosphine Tributyl (tetradecyl) phosphonium chloride Trioctyl (octadecyl) phosphonium iodide catalyst, phase-transfer Tetraethylammonium chloride Tetraoctylphosphonium bromide Tri-n-butyl methyl ammonium chloride Tri methyl phenyl ammonium hydroxide catalyst, phenolics Triethylamine... 

ClgHgyNyPjSift, Methyl-[tris(dimethylamino)phosphonium]amino -tris-(trimethylsilyl-amino)-trimethylsilyl-iminophosphoranide, 456, 751 C20H13O4P, 1-Phenyl-1,1 -spirobi(3H-2,1-benzoxaphosphole)-3,3 -dione, 446, 627... 

C2 2H3 2N2O6P2, trans-1,3-Di-p-tolyl-2,4-diethoxy-2,4-bis(ethylenedi-oxy)-1,3,2X ,4X -diazaphosphetidine, 43B, 872 C22H35INO5P, Phenyl-(a-hydroxycyclohexyl)-phosphonic acid N-methyl-N-phenylaminoethyl ester methiodide dihydrate, 43B, 873 C22H36CIN4O6P, 4-Nitrobenzyl-tris(piperidino)phosphonium perchlorate, 46B, 680... 

Arylation of Quinoline N-Oxides and Pyridines N-Oxides. An efficient protocol to directly arylate quinoline A-oxides was developed using palladium acetate as the catalyst and potassium carbonate as the hase. A survey of different phosphines demonstrated that the sterically less encumbered di-tert-butyl(methyl)phosphonium tetrafluoroborate provides higher yields relative to tri-iert-hutylphosphine. Using this protocol, 15 quinohne A-oxides were arylated in good to excellent yields (eq 1). ... 

A similar protocol for the arylation of isoquinohne A-oxides has been described. A screen of different phosphines showed that di-tert-butyl(methyl)phosphonium tetrafluorohorate provides a greater regioselectivity in favor of the Cl-arylated compound than tricyclohexyl or tri-terf-butylphosphine (eq 2). 

Di-tert-butyl(methyl)phosphonium tetrafluorohorate also provides higher regioselectivity than tri-iert-hutylphosphine in the arylation of pyridine A-oxides (eq 3). 

Di-terr-butyl(methyl)phosphonium tetrafluoroborate was demonstrated to give a better yield of the arylated product than tri-fert-butyl(phosphonium) tetrafluoroborate in the palladium-catalyzed C-H activation of pyridine (V-oxide with Al-acetyl 2-bromo-4-methylaniline (eq 11). ... 

Applications of these C-H activation processes in polymerization reactions have also been reported in the literature. For example, a palladium-catalyzed C-H arylation polycondensation was carried out between a thiophene unsubstituted at the 2- and 5- positions and its 2,5-dibromo derivative. The transformation was effected in the presence of palladium acetate, a phosphine, and cesium carbonate in DMF at 100 °C for 48 h (eq 23). A survey of different phosphines showed that similar yields, molecular weights (Mn), and polydispersity indexes (PDI) could be obtained using di-tert-butyl(methyl)phosphonium tetrafluoroborate or tri-cyclohexylphosphonium tetrafluoroborate as the ligand. ... 

The selective activation of the primary hydroxyl group in methyl a-D-glucopyranoside by reaction with carbon tetrachloride and tris(dimethylamino)phosphine in A/.N-dimethylformamide at —40° has been reported.381 An alkoxytris(dimethylamino)phosphonium... 

X-Ray.—The crystal and molecular structure of tri-o-tolylphosphine, its oxide, sulphide, and selenide (125) have been compared. The mean P—C bond lengths appear to be determined by the n-electron density along the P—C bond and intramolecular steric interactions, d-Orbital participation was considered to be of little importance.152 X-Ray diffraction established the structure of diphosphinofumarate (126)153 and showed that the phospholanium iodide (127) has an envelope ring with the methyl group at the point of the flap.154 The bicyclic phosphonium bromide (128) has a distorted half-chair phosphorus-containing ring, one of the P—C bonds in the... 

Phosphonium (Bromo-difluoro-methyl)-tris-[diniethylamino]-ElOb,. 441 (Educl)... 

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