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Chemfiles Volume 5 Article 1

Although the aziridinations1 and aminohydroxylations2 of olefins using chloramine-T as a commercially-available and inexpensive nitrene source have been well documented, the use of chloramine-T in other capacities as an oxidizing agent is less well-known.

When a solution of chloramine-T in acetonitrile was added to thioglycosides, it resulted in their chemoselective hydrolysis into glycosyl hemiacetals under neutral conditions (Scheme 36). The reaction is carried out without requiring any additive, and is tolerant of a variety of functional groups. Furthermore, neither oxidation of sulfur atoms, nor formation of aziridines was observed during the course of the reaction.3

Scheme 36

Chloramine-T is also capable of oxidative cyclization to produce various heterocycles. A recent report details the synthesis of 1,2,4-triazolo[4,3-a][1,8]naphthyridines using chloramine-T under microwave irradiation (Scheme 37). The reaction proceeds cleanly in minutes, and requires a simple mild work-up to obtain the desired product.4

Scheme 37

Fused cyclic ethers have been obtained through oxidation by chloramine-T. Pyranocyclohexane derivatives were synthesized starting from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, using chloramine-T in a key step on an oxime derivative (Scheme 38).5

Scheme 38

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  1. Some recent examples: (a) Kumar, G. D. K. and Baskaran, S. Chem. Commun. 2004, 1026; (b) Minakata, S. et al. Angew. Chem. Int. Ed. Engl. 2004, 43, 79; (c) Kantam, M. L. et al. Tetrahedron Lett. 2003, 44, 9029; (d) Kano, D. et al. J. Chem. Soc. Perkin Trans. 1 2001, 3186; (e) Brandt, P. et al. J. Am. Chem. Soc. 2000, 122, 8013–8020; (f) Jeong, J. U. et al. J. Am. Chem. Soc. 1998, 120, 6844.
  2. (a) Rudolph, J. et al. Angew. Chem. Int. Ed. Engl. 1996, 35, 2810; (b) Li, G. et al. Angew. Chem. Int. Ed. Engl. 1996, 35, 451; (c) Li, G. and Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649.
  3. Misra, A. K. and Agnihotri, G. Carbohydrate Research 2004, 339, 885.
  4. Mogilaiah, K. and Reddy, G. R. J. Chem. Res. 2004, 145.
  5. Pal, A. et al. Tetrahedron 1999, 55, 4123.

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