Phenyltrimethylammonium toluene

Phenyltrimethylammonium Ion, N+(CH3)S-CaHe.—In this ion, as in toluene, we ignore the electrons involved in bonds from nitrogen to the attached groups, and consider only the inductive effect. The positive charge on the nitrogen atom increases its electron affinity to a value still greater than that for neutral nitrogen, so that we... 

By introducing reasonable values (about 2 for nitrogen, 4 for oxygen) for the electron affinity parameter relative to carbon, 8, and for the induced electron affinity for adjacent atoms (32/8i = Vio), we have shown that the calculated permanent charge distributions for pyridine, toluene, phenyltrimethylammonium ion, nitrobenzene, benzoic acid, benzaldehyde, acetophenone, benzo-nitrile, furan, thiophene, pyrrole, aniline, and phenol can be satisfactorily correlated qualitatively with the observed positions and rates of substitution. For naphthalene and the halogen benzenes this calculation does not lead to results... 

A. Phenyltrimethylammonium Sulfomethylale. A solution of 24.8 g. (26 ml., 0.2 mole) of freshly distilled dimethylaniline (Note 1) in 100 ml. of toluene (Note 2) is prepared in a 250-ml. Erlenmeyer flask which is equipped with a thermometer and a magnetic stirrer. The mixture is stirred and heated to about 40°. The heating is stopped and 19 ml. (0.2 mole) of distilled dimethyl sulfate (Note 3) is added through an addition... 

Although sodium amalgam is unreactive toward phenyltrimethylammonium chloride, benzyltrimethylammonium chloride is cleaved to toluene and trimethylamine. A similar reaction is responsible for the reductive ring opening of N, N-dimethyltetrahydroquinolinium chloride to 2-propyl-A, A-dimethylaniline [123]. 

A rapid method for resolving ( + )-carvone through the derivative (151) has been described. Reaction of carvone with allyl Grignard reagents leads to the expected products (152), and these can be aromatized with toluene-p-sulphonic acid to (153) and (154). An improved method for the preparation of carvone 1,3,8-tribromide [(155) see Vol. 1, p. 31] consists in treating the dibromide (156), obtained by Wallach from dihydrocarvone (148), with phenyltrimethylammonium tribromide in tetrahydrofuran. ... 

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