Tetra methyl ammonium iodide

The tertiary amine group in this last compound being more strongly basic than the primary amine group in amino acetic acid would more readily form an inner ammonium salt. There is also a tetra-methyl ammonium iodide compound formed analogous to the tetra-methyl ammonium salts of the alkyl amines. 

With acids this salt loses potassium iodide, KI, and yields an acid. This acid has the constitution of an inner salt and would be related to what we may term the normal tetra-methyl ammonium iodide acid, by the loss of hydrogen iodide, and to a tetra-methyl ammonium... 

With potassium iodide it yields the corresponding iodide (C6H6)2=I—I, di-phenyl iodonium iodide, which is analogous to the quaternary tetra-methyl ammonium iodide. 

Tetra-methyl ammonium acetic acid iodide normal acid)... 

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... 

Another class of esterification reagents are halogenated compounds (alkyl iodides, substituted benzyl, and phena-cyl bromides), which need basic media for their reaction [K2CO3 or DMFA (dimethyl formamide) is normally used for the neutralization of HHal as acid by-product]. For methy-lation of carboxylic acids, some tetra-substituted ammonium hydroxides or halides can be used, e.g., tetramethylammo-nium hydroxide (in aqueous solutions) or trimethylanilinium hydroxide (in methanol solution). The intermediate ammonium carboxylates are thermally unstable and produce methyl alkanoates when the reaction mixtures are heated or when the carboxylates are introduced into the hot injector of the gas chromatograph (flash or on-column methylation) ... 

Ketones. N,N-Dimethyldithiocarbamylacetonitrile treated 3-6 hrs. at room temp, with methyl iodide in aq. 50%-NaOH containing catalytic amounts tetra-n-butyl-ammonium iodide a-(N,N-dimethyldithiocarbamyl)propionitrile (Y 82%) allowed to react 10-40 hrs. with amyl bromide under the above phase transfer conditions dialkylated intermediate (Y 94%) treated 1 hr. at room temp, with N-bromosuccinimide in aq. 40%-acetonitrile followed by treatment with aq. NaOH for 0.5 hr. product (Y 88%). F. e., also cleavage with aq.-alc. NaOH, s. Y. Masuyama, Y. Ueno, and M. Okawara, Tetrah. Let. 1976, 1961 review of phase transfer catalysis s. E. V. Dehmlow, Ang. Ch. 59, 521 (1977). 

The following chemicals were used as received (from Aldrich unless otherwise noted) 2,6-diaminoanthraquinone, 2,5-dichloro-p-phenylenediamine, 2,6-diamino-5-nitropyrimidine, 2,3,5,6-tetra-methyl phenylenediamine, 2,6-diamino-8-purinol hemisulfate monohydrate, adenine (Chemalog Chemical Dynamics Corp.), 1,9-diamino-nonane, 4,4 -diaminodiphenyl sulfon (Fluka AG), 4,4 -methylene-dianiline, tetraphenyl phosphonium iodide, tetrabutyl ammonium iodide, tetramethyl ammonium bromide, dibenzo-l8-crown-6, 15-crown-5, triphenylantimony dichloride and triethylamine (Eastman Kodak Co.). 

Sulfoxides without amino or carboxyl groups have also been resolved. Compound 3 was separated into enantiomers via salt formation between the phosphonic acid group and quinine . Separation of these diastereomeric salts was achieved by fractional crystallization from acetone. Upon passage through an acidic ion exchange column, each salt was converted to the free acid 3. Finally, the tetra-ammonium salt of each enantiomer of 3 was methylated with methyl iodide to give sulfoxide 4. The levorotatory enantiomer was shown to be completely optically pure by the use of chiral shift reagents and by comparison with a sample prepared by stereospecific synthesis (see Section II.B.l). The dextrorotatory enantiomer was found to be 70% optically pure. 

Stannous octoate Stearamide MEA Stearyl methacrylate 3-(N-Styrylmethyl-2-aminoethylamino) propyltrimethoxysilane hydrochloride Sucrose distearate Sulfated neatsfoot oil Sulfated olive oil Synthetic wax Talc Tall oil Tallowamide DEA Tallowamine acetate Tetra-n-butoxysilane Tetrakis (2-ethoxyethoxy) silane Tetrakis (2-methoxyethoxy) silane Tetramethoxysilane 2,2,4,4-TetramethyM, 3-cyclobutanediol 1,1,4,4-Tetramethyldichlorodisilethylene 1,1,3,3-Tetramethyldisiloxane Tetramethylsilane Tetramethylthiuram disulfide Tetra-n-propoxysilane Tributoxyethyl phosphate Tributyl phosphate Trichlorosilane Triethoxysilane N-[3-(Triethoxysilyl)-propyll 4,5-dihydroimidazole N-(Triethoxysilylpropyl) urea Triethylchlorosilane Triethyl phosphate Triethylsilane Trilauryl trithiophosphite Trilinoleic acid 1-Trimethoxysilyl-2-(chloromethyl) phenylethane Trimethoxysilylpropyidiethylene triamine N-Trimethoxysilylpropyl-N,N,N-trimethyl ammonium chloride Trimethylethoxysilane 2,6,8-Trimethylnonyl-4-alcohol Trimethylolpropane tricocoate 2,2,4-Tri methyl-1,3-pentanediol Trimethylsilyl acetamide o-Trimethylsilyl acetate Trimethylsilyl imidazole Trimethylsilyl iodide Trimethylsilyinitrile Trimethylsilyl trifluoromethane sulfonate Vermiculite Vinyidimethylchlorosilane ... 

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