Organic Lab Reactions 275

Organic Lab Reactions 275 - deamination procedure to amino...

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270 THE AROMATIC PRIMARY AMINO GROUP into compounds known as diazo oxides or diazophenols (XIII, XIV), either spontaneously or under the influence of alkali.* XIV Replacement of the diazo group by hydrogen has been reported for a number of diazo oxides. For example, the diazo oxide from 2-nitro-4- aminophenol yields o-nitrophenol in 53% yield, 42 - ** and that from 1- anuno-2-hydroxy-6-bromonaphthalene-4^sulfonic acid gives XV in ap- proximately 50% yield. 44 NH 2 N 2 ,—OH SO 3 H Once again, the data are so sparse that generalized statements are not justified. m Apparently, very few attempts have been made to apply the ethanol
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Unformatted text preview: deamination procedure to amino ethers. It is of interest to note that, * For a discussion of the structure of the diazo oxides (diazophenols) see Sidgwick, "The Organic Chemistry of Nitrogen," revised by Taylor and Baker, pp. 422-423, Oxford Uni-versity Press, 1937. For convenience, the first of the two resonance structures (XIII, XIV) will be used in this chapter. " JQemenc, Ber., 47, 1413 (1914). " Morgan and Porter, J. Chem. Soc., 107, 652 (1915). "Ruggli and Michels, Hdv Chim. Ada, 14, 781 (1941)....
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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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