Aziridination of alkenes using N-iodo-N-potassio-p-toluenesulphonamide as a nitrene precursor

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 575-577

  Jain, Suman L ^a   Sain, Bir ^a  

^a CSIR INDIAN INSTITUTE OF PETROLEUM   (India)

Author keywords

Aziridination; Bromamine T; Chloramine T; N iodo N potassio p toluenesulphonamide; Nitrenes

Indexed keywords

ALKENE DERIVATIVE; COPPER; N IODO N POTASSIO 4 TOLUENESULFONAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0037433943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02582-0     Document Type: Article

References (27)

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26. Preparation of N-iodo-N-potassio-p-toluenesulphonamide: 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 vacuum at 100°C and could be stored in a dessicator over calcium chloride for a long period without any decomposition. {E. Viel. Fr. 1950, 957,036. (CA, 46:9599h)}.
27. 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 mmol) and powdered 5 Å molecular sieves (100 mg) under a nitrogen atmosphere at 25°C. Stirring was further 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.