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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 1
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Original Articles

An Unusual Copper Catalyzed Iodine Mediated Aziridination of Olefins with the Direct Use of p‐Toluenesulphonamide

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Pages 9-13 | Received 24 Sep 2004, Published online: 05 Aug 2006
 

Abstract

p‐Toluenesulphonamide/I2 was found to be an efficient system for the copper catalyzed aziridination of olefins in good yields under very mild conditions.

Notes

1 Typical experimental procedure: To a stirred mixture of Cu (OTf)2 (18 mg, 5 mol%) and 4‐methylstyrene (118 mg, 1 mmol) in acetonitrile (5 mL) was added p‐toluenesulphonamide (205 mg, 1.2 mmol), iodine (303 mg, 1.2 mmol) and powdered 5Å molecular sieves (100 mg) under a nitrogen atmosphere at 25°C. Stirring was further continued for 3.5 h. The reaction progress was monitored by TLC (SiO2) using ethylacetate/hexane (4:6) as solvent system. After completion, solvent was evaporated under reduced pressure. The residue obtained was purified by passing through a short silica gel column using hexane/ethyl acetate (4:6) as eluent. Evaporation of the solvent yielded N‐(p‐tolylsulphonyl)‐2‐(p‐methylphenyl)aziridine (Yield 230 mg, 80%). IR νmax (cm−1) 3034, 1600, 1516, 1360, 1158; 1H NMR (δ ppm) 2.30 (s, 3H), 2.36 (d, J = 4.2 Hz, 1H), 2.42 (s, 3H), 2.96 (d, 7.16 Hz, 1H)), 3.73 (dd, 7.16, 4.2 Hz, 1H), 7.33–7.09 (m, 6H), 7.87 (d, 2H). Similarly other aziridines were prepared.

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