Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Reaction of N-Haloamide. XIII. The Coupled Reaction of N, N-Dibromobenzenesulfonamide and Formamide or Dimethylformamide with Cyclohexene
SHOJI TAKEMURAHATSUMI NIIZATOYOSHIO UENO
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1971 Volume 19 Issue 8 Pages 1606-1610

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Abstract
The reaction of N, N-dibromobenzenesulfonamide (I) with cyclohexene (II) in formamide or dimethylformamide were studied. The reaction of I with II in formamide gave a major product, trans-2-bromo-1-cyclohexyl N-benzenesulfonylformimidate (III), and minor products, trans-1, 2-dibromocyclohexane (IV), trans-2-bromocyclohexyl formate (V), trans-2-bromocyclohexanol (VI) and benzenesulfonamide (VII).
The reaction in dimethylformamide, contrary to that in formamide, gave another type of product, N, N-dimethyl-N'-benzenesulfonylformamidine (IX), IV, V and VI were also obtained as by-products.
The mechanism to form these products was discussed.
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© The Pharmaceutical Society of Japan
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