Organic Lab Reactions 273

Organic Lab Reactions 273 - dinitrotoluene in yields...

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268 THE AROMATIC PRIMARY AMINO GROUP NOj NO* •NH 2 VIII It is significant that, on treatment with water, pentabromobenzene- diazonium acid sulfate does not yield the expected phenol. Instead, part of the salt is converted into pentabromobenzene and part is resinified.* 2 The nitro group exerts a powerful influence in facilitating the reduction of diazonium salts by alcohols. 22 - ** With ethyl alcohol little, if any, ether is formed. 83 In addition to minimizing ether formation, the pres- ence of a nitro group tends to decrease the amount of tar produced. Consequently nitro substituted amines are frequently susceptible of deamination in excellent yields; this is especially true when several nitro groups are present. Thus, 3-nitro-4-aminotoluene is converted to m- nitrotoluene in 67% yield, 34 p-nitroaniline gives nitrobenzene in approxi- mately 70% yield, 22 and 3,5-dinitro-4-aminotoluene is converted to 3,5-
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Unformatted text preview: dinitrotoluene in yields approaching the theoretical. 36 Other typical examples are the deaminations of 2,4-dinitro-l-naphthylamine (50% yield), 36 of the trans dinitroaminostilbene (IX) in 56% yield, 87 and of the dinitrodimethylbenzidine (X) in 53% yield. 88 NO 8 NOj C=C H \ IX NO* One of the rare instances of failure to deaminate a nitroamine was reported in 1875; 39 despite repeated attempts, m-nitrotoluene could not 82 Hantzsch and Smythe, Ber., 33, 505 (1900). "Orndorff and Cauffman, Am. Chem. J., 14, 45 (1892). 84 Clarke and Taylor, Org. Syntheses, Coll. Vol. I, 415, 1941. 86 Cohen and McCandlish, J. Chem. Soc, 87, 1271 (1905). 86 Hodgson and Walker, J. Chem. Soc., 1933, 1620. "Ruggli and Dinger, Helv. Chim. Aeta, Hi, 182 (1941). 88 Case and Koft, J. Am. Chem. Soc, 63, 510 (1941), " L&denburg, Ber., 8, 1212 (1875)....
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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