N-Methyl-p-toluidine

The typical systems are BPO-DHET(N,N-di(2-hy-droxyethyl)-p-toluidine) system, BPO-DHPT(N,N-di(2-hydroxypropyl)-p-toluidine) system, BPO-HMA(N-2-hydroxyethyl-N-methyl-aniline), and BPO-HMT(N-2-hydroxylethyl-N-methyl-p-toluidine) system [17-19]. Their polymerization rate and overall activation energies of polymerization Ea are determined and the data are compiled in Table 2. 

Similar results were obtained in the photografting reaction of N-methyloyloxethyl-N-methyl-p-toluidine... 

The Ru(II)/ROOH system can also be used to oxidize tertiary amines. The intermediate iminium ion is formed, as described earlier for secondary amines, and can be trapped by nucleophiles. Thus, the ruthenium-catalysed oxidation of tertiary amines with hydrogen peroxide in methanol can be performed to give the corresponding a-methoxyamines with high efficiency as illustrated in Fig. 24 [ 137]. Another example is the selective demethylation of tertiary amines in methanol with a combination of Ru(II) and H202, followed by hydrolysis of the intermediate a-methoxylated amines. For example, the methoxylation of N,N-dimethyl-p-toluidine followed by treatment with 2 N HC1 solution gave N-methyl-p-toluidine in 75% yield (Eq. 35) [137]. 

Fig. 5.5. GC separation of TFA derivatives of arylamines. Peak 1 = solvent (CH2CI2) 2 = N-methyl-aniline 3 = N,N-dimethylaniline 4 = N-ethylaniline 5 = N-methyl-o-toluidine 6 = N-methyl-m-toluidine 7 = N-methyl-p-toluidine 8 = o-toluidine 9 = o-ethylaniline 10 = aniline 11 = 2,5-dimethyl-aniline 12 = 2,6-dimethylaniline 13 = 2,4-dimethylaniline 14 = m- toluidine 15 = p-toluidine 16 = 2,3-dimethylamline 17 = 3,5-dimethylaniline 18 = m-ethylaniline 19 = p-ethylaniline 20 = 3,4-dimethylaniline. Conditions stainless-steel column, 18 ft. X 0.125 in. O.D., 9.5% Apiezon L + 3.6% Carbowax 20M on Aeropack 30 (80—100 mesh) helium flow-rate, 100 ml/min column temperature, 152°C. (Reproduced from Anal. Chem., 39 (1967) 1188, by courtesy of the American Chemical Society.)...

Materials. 2, 3-dinitroaniline (8), -methyl-N, N-dimethyl-aniline (9), p-chloro-N, N-dimethylaniline (9), p-nitro-N, N-dimethylaniline (1 ), N-methyl-p-toluidine (11), p-chloro-N-methylaniline (11), N, 2, 4-trinitroaniline (12), 2, 4-dinitro-N-methylaniline (13), 2, 4-dinitro-N, N-dimethylaniline (13) and N, 2, 4-trinitro-N-methylaniline (14) were prepared by known methods. Spectroscopic grade nitromethane and methylene chloride were dried using a molecular sieve. The other substrates were either available from related studies or were purchased and purified by standard methods. 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Ethy Ibenzy lamine A -Methyl o-toluidine A -Methyl m-toluidine. 2V-Methyl p-toluidine A -Ethyl o-toluidine -Ethyl m-toluidine -Ethyl p-toluidine 2V-Methyl a-naphthylamine 2V-Methyl p-naphthylamine 2V-Phenyl- a-naphthylamine N-Phenyl- p-naphthylamine... 

Matsson and co-workers (Axelsson et al., 1987) measured the carbon-ll/carbon-14 a-carbon KIEs for the Menshutkin reaction between N,N-dimethyl-p-toluidine and labelled methyl iodide in methanol at 30°C. The 1 -labelled methyl iodide required for this study was prepared in three steps [reaction (23)] from the "C atoms produced in a cyclotron (L ngstrom etal., 1987). 

V-Ethylbenzylamine A -Methyl o-toluidine TV-Methyl m-toluidine. A7-Methyl p-toluidine A7-Ethyl o-toluidine A7-Ethyl m-toluidine A7-Ethyl p-toluidine A7-Methyl a-naphthylamine. . ZV-Methyl p-naphthylamine. 2V-Phenyl-a-naphthylamine. N-Phenyl- p-naphthylamine. ... 

It is noteworthy that metallation of N,N-dimethyl-p-toluidine takes place at the position ortho to the dimethylamino group rather than on or ortho to the aryl methyl group. Appar-... 

Others 1,4-dioxane, 1,3,5-trioxane, terahydrofuran, 2-butyl tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, epsilon-caprolactam, benzothiazole, biphenyl, pyrazine, 2-butanone oxime, l-methyl-2-pyrrolidone, N,N-dimethyl-aniline, N,N-dimethyl-p-toluidine, l-methyl-7-isopropyl phenanthrene, dibenzyl-amine, hexamethylenetetramine, squalene, 2-ethylanthraquinone... 

S830). Use of the N-nitro derivative 152 (R = NOz) gave the N-nitro-diazocines 153 (R = N02 R1 = H, Me) (83S830). There have been two reports of reaction of Af-methyl-p-toluidine with acidic formaldehyde solution to yield the diazocine 67 (R -R3 = H, R4 = R5 = Me) (76CI(L)1644). Similarly, reaction of formaldehyde with diphenylamine afforded... 

Olefins, synthesis -Butyllithium. 1,3-Dibenzyl-2-methyl-l, 3,2-diazaphospholidine. Dimethyl methylphosphonothioate. Diphenylsulfonium isopropylide. N-Methanesulfinyl-p-toluidine. Methylphosphoric acid bis(dimethylamide). Phosphoryl chloride-Stannous chloride-Pyridine. p- Toluenesulfonylhydrazine. Triphenyl phosphite. 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline AT-Methylbenzylamine N -Ethy Ibenzy lamine AT-Methyl o-toluidine M-Methyl m-toluidine iV-Methyl p-toluidine Al-Ethyl o-toluidine N-Ethyl TO-toluidine N-Ethyl p-toluidine A -Methyl a-naphthylamine A -Methyl p-naphthylanaine A -Phenyl- a-naphthylanaine Af-Phenyl- p-naphthylamine... 

Dimethyl ethanolamine Dimethyl lauramine Dimethyl palmitamine Dimethyl stearamine N,N-Dimethyl-p-toluidine Dipropylenetriamine Dodecenylsuccinic anhydride 2-Dodecen-1-ylsuccinic anhydride Ethylamine Ethylenediamine 2-Ethyl-4-methyl imidazole Hexadecenyl succinic anhydride Hexamethylenediamine Imidazole 1,8-p-Menthanediamine Methyidiethanolamine 4,4 -Methylenedianiline Methyl hexahydrophthalic anhydride Methyl himic anhydride 2-Methyl imidazole 2-Methylpentamethylenediamine 3-Methylpiperidine Nonenyl succinic anhydride Octadecenyl succinic anhydride Octenylsuccinic anhydride N-Oleyl-1,3-propanediamine... 

N-ife see.2 3-DinitrOri7-methyl.p-toluidine. N Acetyl 2 3- dinitro -p acet - toluidide. 

N-Jfe see 3 d-Dinitro-iv-methyl-p-toluidine. IH-Acetyl 3 d-duutro-p-ac t-tolmdide. M.p. 196°. 

Di-/ -butyl phthalate 4-Methylacetanilide, p-Toluidine Methyl acetate, see Methvl tert-butvl ether Methylacetoacetate, see Mevinphos o-Methylacetophenone, see o-Xylene /n-Methylacetophenone, see ro-Xylene p-Methylacetophenone, see p-Xylene... 

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