ChemInform Abstract The reactivity of the title compounds, i.e. the highly electrophilic sulfonamides (I) and (VI) and carboxamides (VIII), is investigated. (I), on reaction with the primary amines (II), affords the unstable adducts (III), whereas the more basic secondary amines (IV) cause cleavage of CHCl3 from (I) or (VI) and formation of the formamidines (V) or (VII), respectively. The carboxamide (VIII), on reaction with secondary amines such as e.g. diethylamine (IVa) or on reaction with ethanol-N,N-dimethylamine (X), affords the stable adducts (IX) or (XI), respectively.
174ChemInform Abstract The reaction between the N,N-dichloroarylsulfonamides (I) and trichloroethene (II) yields the arylsulfonylimines (III). These react in situ with benzaldazine (IV) to give the 1,3,5,7-tetraazabicyclo(3.3.0)octanes (V). The formation of these proceeds via two steps: formation of a 1:1 adduct of (III) and (IV) and cyclization of the dipolar adduct to give a triazole intermediate, which is stabilized by the addition of a second molecule of (III) to give the corresponding tetraaza compound (V). The reaction described here constitutes the first example of a reaction between a highly electrophilic arylsulfonylimine and an aldazine.
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