Bis-quaternary ammonium salts

Barlow RB, Ing HR (1948) Curare-like action of polymethylene bis-quaternary ammonium salts. Br 1 Pharma Chemother 3 298-304... 

Bis-quaternary ammonium salts have also been used Lissel, M. Feldman, D. Nir, M. Rabinovitz, M. Tetrahedron Lett. 1989, 30, 1683. 

Zheng, F Bayram, E Sumithran, S.P., Ayers, J.T., Zhan, C.-G., Schmitt, J.D., Dwoskin, L.P. and Crooks, P.A. (2006) QSAR modeling of mono-and bis-quaternary ammonium salts that act as agonists at neuronal nicotinic acetylcholine receptors mediating dopamine release. Bioorg. Med. Chem., 14, 3017-3037. 

Ancelin, M. L., Calas, M., Bonhoure, A., Herbute, S., and Vial, H. J. (2003). In vivo antimalarial activities of mono- and bis quaternary ammonium salts interfering with Plasmodium phospholipid metabolism. Antimicrob. Agents Chemother. 47,2598-2605. 

Effect (4) emerged in other classes of bis-quaternary ammonium salts,... 

The high-pressure reaction of a,w-tertiary diamines with a,w-diiodo compounds gave an almost quantitative yield of the macrocyclic bis quaternary ammonium salts (method E-15) (Jurczak and Pietraszkiewicz, 1985 Jurczak et al., 1989). The macrocyclic bis quaternary ammonium salt was demeth-ylated with triphenylphosphine to give the A, A -dimethyldiaza-crowns in good... 

Tertiary amines have been cyclized with diiodides under high pressure (10 kbar) to produce a macrocyclic bis quaternary ammonium salt (method U-21) (Jurczak et al., 1989). The methyl groups were removed using tri-phenylphosphine. The cyclization reaction gave high yields even when using... 

C Tetrafluoro-p-xylene Bis-quaternary ammonium salt Europe 200... 

Subsequently, Itsuno s group [38] further disclosed a main-chain-functionalized polymer via a similar strategy. Mixing aqueous solution of bis(quaternary ammonium salt) and disulfonate salts led to the formation of a chiral polymer (18) bearing ionic bonds in the main chain (Figure 4.15). The catalytic ability of this ionic polymer was tested in the benzylation of N-diphenylmethylene glycine tert-butyl ester increased enantioselectivity albeit with lower activity was observed. In addition, the catalyst could be easily recovered and reused without loss of activity and enantioselectivity for three runs. 

A new ionic polymeric polycarbamate was synthesized after steps of polyurethane chemistry using 3-iso-cyanatemethyl-3,5,5-trimethylcyclohexyl isocyanate, 2,5-dimethyl-2,5-dihydroperoxyhexane, 1,6-butanediol, 2,4-tolylenediisocyanate, and N,N -bis(j3-Hydroxy-ethyOpiperazine [27]. Modification of the nitrogen of the piperazine ring into quaternary ammonium salt by treatment with methyliodide gave the MPI high electroconductivity. 

Recently, there has been much interest in developing water-soluble tributyltin biocides to lessen the costs of application, and to prevent fire hazards when treating material in confined spaces. Bis(tributyltin) oxide itself has a very low aqueous solubility ( 0.001%), but it may be made water-dispersible by the addition of certain (534, 535) quaternary ammonium salts. Formulations of this type, although currently under development as wood preservatives (534), have been used extensively in the United Kingdom for the treatment of stonework to eradicate fungal growths, algae, mosses, and lichens (535). 

Bis(4- and 3-hydroxyphenyl)-l,3,4-oxadiazoles were alkylated in an excess of epichlorohydrin in the presence of NaOH and quaternary ammonium salts, while the temperature was gradually raised from 20 to 90 °C, affording luminescent epoxide monomers (Scheme 17) <1999CHE358>. 

Surface disinfectants Compounds containing phenolics, chlorhexidine (not effective against bacteria spores), quaternary ammonium salts (additional activity if bis-n-tributyltin oxide present), hypochlorites such as household bleach, alcohols such as 70-95% ethanol and isopropyl (not effective against bacteria spores), potassium peroxymonosulfate, hydrogen peroxide, iodine/iodophores, and triclosan. 

The catalysed alkylation of l//,4//-pyrazol-5-ones is solvent dependent. In benzene, bis-alkylation occurs at the 4-position whereas, in a carbon disulphide benzene mixture, O-alkylation is observed, although the major product (4, Scheme 5.22) results from nucleophilic attack by the pyrazolone on the carbon disulphide, followed by alkylation of the dithiolate dianion [92]. The catalysed reaction of 2-thiono-3-aryl-thiazolidin-4-ones with alkylating agents under soliddiquid two-phase conditions results in alkylation at the 5-position (60-80%) [93]. The aldol condensation of the thiazolidinones with aryl aldehydes is also catalysed by quaternary ammonium salts. 

The use of cerium(IV) salts as catalytic oxidation mediator is restricted by their insolubility in non-aqueous media. Cerium(IV) ammonium nitrate (CAN) may be used in organic solvents upon the addition of quaternary ammonium salts, but cerium(IV) sulphate is not transferred under analogous conditions. Bis(tetra-/t-butyl-ammonium) hexanitratocerate(IV) is obtained in a solid form by metathesis of CAN... 

Cetyltrimethyl ammonium bromide (CTAB) dodecyltrimethyl ammonium bromide (DTAB) tetradecyltrimethyl ammonium bromide (TTAB) trioctyl-methyl ammonium chloride (TOMAC) N-benzyl-N-dodecyl-hf-bis(2-hy-droxy ethyl) ammonium chloride (BDBAC) cetyl pyridinimn chloride (CPC) quaternary ammonium salt with carbon atoms of R ranging from 8-10 (CHj Rj N+ CL) (Aliquat 336)... 

The importance of solvents and their effects play roles in electrochemistry as well. The properties of a family of novel quaternary ammonium salts based on the bis(triflu-oromethylsulfonyl)imide and triflate anions are reported in a paper by Sun (Sun et al., 1998). Binary phase diagrams for some of their mixtures and their electrochemical windows of stability were reported. The highest conductivity observed in the pure salt systems at 25°C was 7 x 10 S cm-1. An electrochemical window of stability of up to 5V was measured on graphite electrodes. The effect of salt structure and solvent on conductivity of the salts is also discussed. 

Scheme 4.2 General synthetic scheme for cinchona-derived dimeric quaternary ammonium salts, (a) bis(Bromomethyl)-linkers (0.5 equiv.), EtOH-DMF-CHCI3 (5 6 2), r.t. or reflux, (b) Allyl bromide or benzyl bromide (6.0 equiv.), 50% KOH (10.0 equiv.), CH2CI2, r.t.

Lygo has extended his asymmetric alkylation methodology to the synthesis of bis-a-amino acids (Scheme 4) [11], Bis-amino acids, such as meso-diaminopirnelic acid, dityrosine and isodityrosine, are found in nature and are thought to act as cross-linking agents which stabilise structural proteins in plants and bacteria. For example, asymmetric alkylation of the Schiff base 3 with the dibromide 13, catalysed by the quaternary ammonium salt le, gave the bis-amino acid derivative 14 in >95% ee. 

The present process is shown schematically in Fig. 15.6. The solution is an emulsion of acrylonitrile and 10-15 per cent disodium hydrogen-phosphate in water containing a quaternary ammonium salt, hexamethylene-bis(ethyldibutylammonium) phosphate, to conduct the current. The anode is carbon steel and the cathode is cadmium (a sheet fixed on to the anode) this cell is a good example of the use of bipolar electrodes (Section 15.3). EDTA and borax are added in small quantities... 

Compound 147 can be considered the prcxluct of bis-phosphonomcthylation of thiazolidine and represents a quite uncommon example of the direct formation of a quaternary ammonium salt in X-alkylation rcactions. ... 

Lygo B, Andrews BI. Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts asymmetric alkylation of glycine imines. Acc. Chem. Res. 2004 37 518-525. 

At very negative potentials neither the tetraalkylammonium ions nor the metallic electrode are inert they combine to form reduced TAA-metals [7]. Tetraalkylammonium (TAA) metals are composed of quaternary ammonium ions, electrons, and a post-transistion metal such as Hg, Pb, Sn, Sb, Bi [5-18] or Pt [19] most of them have the composition R4N" MeJ [13] or R4N" Mc4 [20] and have been described as Zintl ion salts or Zintl phases [21,22]. They have been shown to be useful intermediates in the electrochemical reduction of certain substrates that are reducible with difficulty. On reduction of the quaternary ammonium salt, the initial layer of the metal compound is controlled by a two-dimensional nucleation, whereas the bulk phase is initiated by a three-dimensional nucleation and a growth controlled by the diffusion of R4N from the solution. In some cases (A-methylquinuclidinium (MQ" ) mercury) the catalytic efficiency of the initial layer is greater than that of the bulk phase [18], whereas in other cases (A, A-dimethylpyrrolidinium (DMP" ) lead) the opposite is found [16]. 

Occasionally, a chiral diol can serve as host for one optical isomer (e.g., an epoxide), allowing the other one to be distilled out. The guest optical isomer can then be recovered by stronger heating. A quaternary ammonium salt, derived from the amino acid leucine, has been used to resolve 1,1 - bi-2-naphthol (7.4) by formation of an inclusion compound.57... 

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