Convenient Metal‐Free Aziridination of Alkenes with Chloramine‐T Using Tetrabutylammonium Iodide in Water

Abstract

Tetrabutylammonium iodide was found to be a mild and efficient catalyst for aziridinaton of olefins with chloramines‐T under environment benign conditions.

Keywords:

• Alkene
• aqueous media
• aziridination
• chloramines‐T
• tetrabutylammonium iodide

Notes

^†General procedure for preparation of aziridines: To a mixture of catalyst (0.1 mmol, 10 mol%), chloramine‐T (1.0 mmol), in distilled water (5.0 mL) was added the appropriate olefin (2.0 mmol). The mixture was stirred at room temperature under an ambient atmosphere. The mixture was extracted with ethyl acetate (20 mL×3). The combined organic extracts were dried over Na₂SO₄ and concentrated to give the crude product, which was purificated by column chromatography (silica gel; 20% ethyl acetate in hexane).