Benzvalene and Dewar Benzene Type Sulfinamides

Article abstract of DOI:10.1021/jo00171a024

The reaction of cyclobutadiene aluminum halide ? complexes with N-arylsulfinylamines leads, depending on the substitution pattern of the phenyl ring, to either bicyclic (Dewar benzene type) or tricyclic sulfinamides, the latter being formed via an intramolecular Friedel-Crafts reaction of an intermediate cyclobutenyl cation.A similar reaction of aluminum halide ? complex 1 with N-tert-butylsulfinylamine affords both a bicyclic and a tricyclic (benzvalene type) sulfinamide.