1. Textbooks of organic chemistry allot many pages to substitution reactionsbyamino and related groups, but little is described on the reversed transformation, substitutionofamino and related groups. For example, see:
2. aCarey, F. A.; Sundberg, R. J.Advanced Organic Chemistry,5th ed.Springer:New York, 2007; Part A, pp389−472; Part B, pp215−242.
3. bMcMurry, J.Organic Chemistry,5th ed.Brooks/Cole:Belmont, CA, 2000; pp976−1029.
4. cMorrison, R. T.; Boyd, R. N.Organic Chemistry, 6th ed.Prentice Hall:Upper Saddle River, NJ, 1997; pp821−888.
5. dMalpass, J. R.InComprehensive Organic Chemistry;Barton, D., Ollis, W. D., Sutherland, I. O., Eds.Pergamon Press:Oxford, 1979; Vol.2, pp3−59.In practice, substitution of amino group at ordinary sp3carbon, apart from activated carbon centers such as those at the allylic, benzylic, or acetal position, is usually carried out by its diazotization and quaternarization prior to the substitution. For example, see: