Abstract
Recent achievements in the field of three-dimensional aromaticity (bicycloaromaticity and homoaromaticity) have been reviewed with emphasis on the syntheses of stabilized longicyclic (CH) n ions- bicyclo [3.2.2] nonatrienyl, bicyclo [4.2.1] nonatrienyl, bicyclo [3.3.2] decatrienyl, and bicyclo [4.3.2] undecatetraenyl ions-and the first trishomoaromatic anion-tricyclo [5.3.1.04, 8] undeca-2, 5, 9-trien-11-ide ion. It is now apparent that the predictive power of the three-dimensional aromaticity theory based on Goldstein-Hoffmann' s formulation of ribbon mode remains to be a stimulus guide to the syntheses of organic ions despite its limited experimental manifestation at the present time. (57 references)