Phosphines sulfonic acids

Diphenylmercuryjtert. phosphine Sulfonic acid anhydrides from sulfonic acids s. 19,141... 

Monophosphams. The similar tetrahedral geometry and bond lengths of tetracoordinate phosphoms(V) compared to those of sulfur(VI) suggested that phosphonic and phosphinic acid groups might act as biososteres for the sulfonic acid moiety in the parent monobactams. The... 

Mixed Anhydrides of Phosphoric, Phosphonic, and Phosphinic Acids with Sulfonic Acids... 

A further method for the synthesis of a mixed anhydride between a phosphinic acid and a sulfonic acid employs a sulfonic triazolide ... 

Fig. 9 Zwitterionic nature of the sulfonic acid phosphine ligand...

Scheme 6 Single-pot synthesis of sulfonic acid phosphine ligands...

For the synthesis of carbohydrate-substituted block copolymers, it might be expected that the addition of acid to the polymerization reactions would result in a rate increase. Indeed, the ROMP of saccharide-modified monomers, when conducted in the presence of para-toluene sulfonic acid under emulsion conditions, successfully yielded block copolymers [52]. A key to the success of these reactions was the isolation of the initiated species, which resulted in its separation from the dissociated phosphine. The initiated ruthenium complex was isolated by starting the polymerization in acidic organic solution, from which the reactive species precipitated. The solvent was removed, and the reactive species was washed with additional degassed solvent. The polymerization was completed under emulsion conditions (in water and DTAB), and additional blocks were generated by the sequential addition of the different monomers. This method of polymerization was successful for both the mannose/galactose polymer and for the mannose polymer with the intervening diol sequence (Fig. 16A,B). 

The addition of a proton and a phosphine generally proceeded via cis-addition. When 1-octyne was treated with CH3S03H and PPh3 in acetone- in the presence of Pd(PPh3)4, (Z)-l-deutero-l-octen-2-ylphosphonium salt was obtained (Scheme 9). An H-D exchange occurred between sulfonic acid and the deuterated solvent generating deuterated sulfonic acid, which transferred deuterium to the alkyne. 

These polymers show lower water uptake than the analogous sulfonated poly(arylene ether sulfone) materials, possibly suggesting some interaction between the aromatic nitrile and sulfonic acid. The phosphine oxide functional moiety could also be used as a compatibilizer with other materials. Sulfonated poly(arylene ether phosphine oxide sulfone) terpoly-mers have been prepared both with sulfonated triphenyl phosphine oxide and with triphenyl phosphine oxide with 3,3 -disulfonate-4,4 —dichlorodiphenyl sulfone as the sulfonic acid bearing monomer. Block copolymers containing phosphine oxide appear to avoid the ether—ether interchange that results when non—phosphine oxide blocks are utilized, and this is being further pursued. ... 

Interest in new solid polymer electrolytes has driven some research groups to investigate other materials containing proton conducting moieties aside from sulfonic acid. Polymers and copolymers from monomers containing phosphonic-based proton conductors have been reported. Phosphonic and/or phosphinic acid containing polymers have not been well studied because of the rather limited synthetic procedures available for their preparation, compared with sulfonic acid derivatives. Miyatake and Hay... 

Thiols can be prepared by the reduction of sulfonyl halides652 with LiAIH4. Usually, the reaction is carried out on aromatic sulfonyl chlorides. Zinc and acetic acid, and HI. also give the reduction. Sulfonic acids have been reduced to thiols with a mixture of triphenyl-phosphine and either Ii or a diaryl disulfide.633 Disulfides RSSR can also be produced.634 For the reduction of sulfonyl chlorides to sulfinic acids, see 0-118. 

OjFjPjReSCijH g, Rhenium(l+), tris[l,2-ethanediylbis[dimethylphosphine]-PP ]-, (OC-6-11)-, salt with trifluoromethane-sulfonic acid (1 1), [154419-20-2], 31 254 OjFePjCjTHjj, Iron, tricaibonylbis(diphenyl-phosphine)-, (7B-5-11)-, [40697-11-8], 31 212... 

Potassium triethylborohydride, 260 Sodium borohydride, 21 Ring-forming reactions 2,2 -Dihydroxy-1,1 -binaphthyl, 113 Other asymmetric reactions Camphor-10-sulfonic acid, 62 Di-jjL-chlorobis(l,5-cyclooctadiene)di-rhodium-2,3-0-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenyl-phosphine)butane, 153... 

Sulfonamides may be directly synthesized from sulfonic acid salts by treatment with triphenylphosphine ditriflate followed by an amine <2004JA1024>. This procedure, that avoids the generation of sulfonic acids, converts sulfonic acid salt 129 to sulfonamide 130 in 81% yield (Equation 92). Problems associated with the removal of triphenylphosphine oxide by-products can be alleviated by performing the reaction with polystyrene-supported phosphine. 

The synthesis of sodium trifluoropropenylbenzenesulfonate, (Equation 12) uses the diazo compound obtained from aniline-2-sulfonic acid and isopropyl nitrite in isopropanol for the oxidative addition to palladium(0)/dba, in the absence of phosphine ligands, with NaOAc as buifer. The substrate itself contributes to palladium stabilization (Equation 16). 

The common procedure for adding reactants consists either in simultaneously mixing all the chemical species involved in the reaction, or in allowing the amine and the aldehyde to react first and then adding the substrate. In some cases, however, the condensation of substrate and formaldehyde is carried out first in order to isolate the corresponding methylol derivative, which is subsequently submitted to react with the amine (X-methylation of amino derivatives see Fig. 12) this is advantageous with several substrates, such as nitroalkanes, ferrocenes,- sulfonic acids, and phosphines. ... 

On the other hand, some experimental results are in agreement with the predominance of path b (Fig. 24) they arc due in particular to the aptitude of a very large number of substrates to react readily with aldehydes (see references reported for 12 and Ref. 274). Indeed, several successful syntheses of Mannich bases have been carried out starting from the hydroxymethyl derivative of the substrate, as reported for C-Mannich bases obtained from ferrocenyl derivatives,- nitroalkanes. - and hydrogen cyanide as well as for N-, S-, P-Mannich bases of benzimidazoles, sulfonic acids,- phosphines, etc. 

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