Organic Lab Reactions 294

Organic Lab Reactions 294 - be produced in some cases, the...

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COMPARISON OF VARIOUS DEAMINATION PROCEDURES 289 Although yields were not given, the method was recommended for the replacement of amino groups by hydrogen. 122 It is claimed in a recent patent that ferrous hydroxide is a reagent of considerable value for the deamination of certain aminonaphtholsul- fonic acids. 124 From 3-hydroxy-4-aminonaphthalenesulfonic acid, 90- 96% yields of the naphtholsulfonic acid are reported; the product, how- ever, is not isolated. Aniline gives not only benzene but also phenyl azide and biphenyl in unspecified yields. 123 Alkaline glucose converts the diazonium salts of l-amino-2-hydroxy- naphthalene-4-sulfonic acid and its halogen, nitro, carboxyl, or sulfonic acid derivatives into the corresponding 2-hydroxynaphthalene-4-sul- fonic acids. 126 According to this patent, the yields are nearly quantita- tive. The treatment of diazo compounds with copper hydride affords an- • other means of deamination. 126 ' m> m> 129 Though the hydrocarbon may
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Unformatted text preview: be produced in some cases, the reaction is not very efficient. 128 It is reported that alkaline sodium hydrolumte (Na2S 2 O4) is effective-in converting certain diazo compounds to the hydrocarbons, 119 a state-ment supported solely by reference to the work of Grandmougin. 130 Ac-tually he obtained only a small yield of benzene from benzenediazonium salts but suggested that on further study the process might prove to be useful. Upon reduction with hydrosulfite, the diazo oxide * XXIV is converted to the phenol XXV in 95% yield (crude product.) 131 ' ^ C H S CHs XXIV Further than this, the utilization of sodium hydrosulfite in deaminations apparently has received little attention. COMPARISON OP THE VARIOUS DEAMINATION PROCEDURES Certain generalizations are possible regarding the effectiveness of the various deamination procedures with a particular type of amine. These are noted in the table below. *Seep 270,...
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