S. L. Jain, B. Sain / Tetrahedron Letters 44 (2003) 575–577
577
3. For reviews, see: (a) Lwowski, W. Carbonylnitrenes. In
Nitrenes; Lwowski, W., Ed.; Interscience: New York,
1970; pp. 185–224; (b) Edwards, O. E. Acylnitrenes. In
Nitrenes; Lwowski, W., Ed.; Interscience: New York,
1970; pp. 225–247; (c) Lwowski, W. Acylazides and
Nitrenes. In Azides and Nitrenes, Reactivity and Utility;
Scriven, E. F. V., Ed.; Academic: New York, 1984; pp.
205–246
V. J. Mol. Catal. 2000, 160, 237; (c) Chanda, B. M.;
Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30.
9. (a) Jain, S. L.; Sain, B. Chem. Commun. 2002, 1040; (b)
Jain, S. L.; Sain, B. J. Mol. Catal. 2001, 176, 101; (c)
Sain, B.; Murthy, P. S.; Rao, T. V.; Joshi, G. C. Tetra-
hedron Lett. 1994, 35, 5083.
10. Preparation of N-iodo-N-potassio-p-toluenesulphon-
amide: p-toluenesulphonamide (10 mmol) was dissolved
in KOH (20 mmol) in a minimum amount of water. The
resulting solution was treated with iodine (20 mmol) at
room temperature. Precipitated N-iodo-N-potassio-p-
toluenesulphonamide was filtered on a Buckner funnel
and recrystallized with water. N-Iodo-N-potassio-p-
toluenesulphonamide thus obtained was dried under vac-
uum at 100°C and could be stored in a dessicator over
calcium chloride for a long period without any decompo-
sition. {E. Viel. Fr. 1950, 957,036. (CA, 46:9599h)}.
11. Typical experimental procedure: To a stirred mixture of
CuCl (2.5 mg, 5 mol%) and 4-methylstyrene (295 mg, 2.5
mmol) in acetonitrile (5 ml) was added anhydrous N-
iodo-N-potassio-p-toluenesulphonamide (167 mg, 0.5
4. Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett.
1975, 361.
5. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org.
Chem. 1991, 56, 6744; (b) Evans, D. A.; Faul, M. M.;
Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am.
Chem. Soc. 1993, 115, 5328; (c) Li, Z.; Conser, K. R.;
Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326; (d)
Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am.
Chem. Soc. 1994, 116, 2742; (e) Ilewellyn, D. B.;
Adamson, D. M.; Amdtsen, B. A. Org. Lett. 2000, 2,
4165.
6. Simkhovich, L.; Gross, Z. Tetrahedron Lett. 2001, 42,
8089.
7. (a) Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetra-
hedron Lett. 1998, 39, 309; (b) Vyas, R.; Chanda, B. M.;
Bedekar, A. W. Tetrahedron Lett. 1998, 39, 4715; (c)
Brandt, P.; Sodergren, M. J.; Anderson, P. O.; Norrby, P.
O. J. Am. Chem. Soc. 2000, 122, 8013; (d) Albone, D. P.;
Aujla, P. S.; Taylor, P. C.; Challenger, S.; Derrick, A. M.
J. Org. Chem. 1998, 63, 9569; (e) Ando, T.; Kano, D.;
Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998,
54, 13485.
,
mmol) and powdered 5 A molecular sieves (100 mg)
under a nitrogen atmosphere at 25°C. Stirring was fur-
ther continued for 3 h followed by filtration on a Buchner
funnel. The reaction mixture was then passed through a
small silica gel column using ethyl acetate as eluent.
Evaporation of the solvent yielded an oil which was
purified by column chromatography (silica gel) using
hexane/ethyl acetate (4:1) as eluent. Evaporation of the
solvent yielded N-(p-tolylsulphonyl)-2-(p-methylphenyl)-
aziridine (yield 216 mg, 75%). Similarly other aziridines
were prepared.
8. (a) Vyas, R.; Chanda, B. M.; Bedekar, A. V. Tetrahedron
Lett. 1998, 39, 4715; (b) Vyas, R.; Chanda, B. M.;
Belhekar, A. A.; Patel, D. R.; Ram, R. N.; Bedekar, A.