Aryl(sulfonyl)amino Group: A Convenient and Stable Yet Activated Modification of Amino Group for Its Intramolecular Displacement

Author:

Kato Yuzo1,Yen Dinh Hoang1,Fukudome Yasuhiro1,Hata Takeshi1,Urabe Hirokazu1

Affiliation:

1. Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference52 articles.

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:

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