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Various new structural entities related to X-azatricyclo[m.n.0.0. a,b ]alkanes 15a-d are constructed employing the intramolecular [3+2]-dipolar cycloaddition of nonstabilized cyclic azomethine ylides. The ylides are generated by the sequential double desilylation of N-alkyl-α,α'bis(trimethylsilyl)cyclic amines 14a-d using Ag(I)F as a one-electron oxidant. More rigid azatetracyclo compounds of type 23, in which benzene ring is attached as a tether unit in the Nalkyl chain moiety, are alsodoi:10.3998/ark.5550190.0002.809 fatcat:uaizfwuxsvfghamfrxymu2nolq