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7580056 
Journal Article 
Development of Facile Synthetic Methods Using Heteroatom-Halogen Bonds 
Minakata, S 
2009 
1 
Yuki Gosei Kagaku Kyokaishi
ISSN: 0037-9980 
67 
10 
1001-1011 
WOS:000270864500003 
Heteroatom-halogen bonds were successfully utilized for efficient and convenient synthesis of heterocycles and aminohalogenated compounds from readily available reagents. The direct aziridination of olefins with N-chloro-N-sodio-p-toluenesuffonamide (chloramines-T: CT) in the presence of iodine catalyst has been achieved, and the method was applied to a green process using silica-water as the reaction media. N-Chloro-N-sodiocarbamates reacted with electron-deficient olefins in the presence of a phase transfer catalyst to give the corresponding aziridines, and the method was applied to the asymmetric synthesis. Fullerene, C-60, was also aziridinated by using active reagents containing N-X bonds, and the resulting aziridinofullerenes underwent a unique rearrangement to azafulleroids. Moreover, unique aminohalogenation of olefins utilizing chloramines-T and bromamine-T under an atmosphere of carbon dioxide was also revealed. Treatment of alkenylamides with tert-butyl hypoiodite led to the production of various N-heterocycles. Iodination of readily available sulfonamides or carboxamides with tert-butyl hypoiodite generated reactive N-iodinated amides, which reacted with olefins to give aziridines or oxazolines.