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Organic Lab Reactions 271

Organic Lab Reactions 271 - 18 the meta isomer yields a...

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266 THE AROMATIC PRIMARY AMINO GROUP CH 3 CH 3 Cl-N 8 +- The influence of an ortho methyl group does not completely determine the course of a deamination. One of the early and important examples of the utility of the deamination process^in determining structures in- volved an amino group adjacent to a methyl, namely, the conversion of the leuco base of fuchsine to the diphenyltolylmethane. 17 CH 3 NH 2 In contrast to the ortho and meta isomers, a substantial fraction of p-toluidine can be converted into toluene (45% yield); the ether is also obtained (20% yield). 10 ' 13 A para methyl group apparently facilitates replacement of the diazo group by hydrogen. The influence of the sulfonic acid group upon the course of ethanol deaminations somewhat resembles that of the methyl group. Thus, 0- aminobenzenesulfonic acid gives only the ether;
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Unformatted text preview: 18 the meta isomer yields a mixture of m-ethoxybenzenesulfonic acid and benzenesulfonic acid (the ether predominates); 18-19 and from p-aminobenzenesulfonic acid the only product isolated is benzenesulfonic acid. 20 With the~aminosulfonic acid (VII), in which a methyl group is-para to the amino group, the main product is o-toluenesulfonic acid (59%), and not the ethyl ether (37%) . 21 • CH 3 CH 3 CH S ,SO 3 H I ,SO 3 H I SO3H NH 2 VII " Fischer and Fischer, Ber., 37, 3359 (1904). 18 Franklin, Am. Chem. J., 20, 455 (1898). 19 Shober and Kiefer, Am. Chem. J., 17, 454 (1895). *> Shober, Am. Chem. J., 16, 379 (1893). 11 Remsen and Dashiell, Am. Chem. J., 15, 105 (1893). OCsHg...
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