Investigation on σ-Aromatic and σ-Antiaromatic Compounds

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Reduction of aluminum trichloride-N-heterocyclic carbene adduct with lithium naphthalenide afforded dichloroaluminum radical, the formation of which was evidenced by a trapping experiment. Reduction of N-heterocyclic carbene adduct of dichloroalumane bearing a bulky silyl substituent provided an unexpected compound through migration of an aluminum moiety and elimination of a substituent on the nitrogen atom. Debrominative reactions of1,2-bis(phenylseleno)benzene dibromide with tribromoborane and Ag reagents gave bromoselenonium cation and unexpected selenanthrenium cations, respectively.