Of his many research interests in organic chemistry, including photochemistry with unusual chromophores, synthesis of new carba-/hetera cages, radical cations, dications, total synthesis of aminoglycosid antibiotics, and enzymes, Prinzbach was probably best known for the pagodane route towards dodecahedrane.[citation needed] In the course of his research, the phenomenon of σ-bishomoaromaticity was discovered as an extreme case of chemical bonding. The final landmark the development of dodecahedrane chemistry over many years was the preparation and characterisation of C20 fullerene in the gas phase based on bromination-elimination reactions of dodecahedrane.[1][2]
σ-Bishomoaromaticity
σ-Bishomoaromaticity is an extreme case of the chemical bond and the aromaticity. It was found by the Prinzbach when they synthesized dodecahedrane via the Pagodane route[3][4][5]
^Horst Prinzbach, Andreas Weiler, Peter Landenberger, Fabian Wahl, Jürgen Wörth, Lawrence T. Scott, Marc Gelmont, Daniela Olevano, Bernd v. Issendorff. Gas-phase production and photoelectron spectroscopy of the smallest fullerene, C20. Nature 407, 60-63 (7 September 2000) | doi:10.1038/35024037
^H. Prinzbach, F. Wahl, A. Weiler, P. Landenberger, J. Woerth, L.T. Scott, M. Gelmont, D. Olevano, F. Sommer, B. von Issendorff: C20 Carbon Clusters: Fullerene - Boat - Sheet Generation, Mass Selection, PE Characterization. Chem. Eur. J. 2006, 12, 6268-6280 doi:10.1002/chem.200501611
^G. K. S. Prakash, V. V. Krishnamurthy, R. Herges, R. Bau, H. Yuan, G. A. Olah, W.-D. Fessner, H. Prinzbach. Pagodane dication, a unique 2π-aromatic cyclobutanoid system. J. Am. Chem. Soc. 1986, 108(4), 836, doi:10.1021/ja00264a046.
^G. K. S. Prakash, V. V. Krishnamurthy, R. Herges, R. Bau, H. Yuan, G. A. Olah, W.-D. Fessner, H. Prinzbach. [1.1.1.1]- and [2.2.1.1]Pagodane dications: frozen two-electron Woodward-Hoffmann transition-state models. J. Am. Chem. Soc. 1988, 110(23), 7764, doi:10.1021/ja00231a029.
^R. Herges, P. v. R. Schleyer, M. Schindler, W.-D. Fessner. Tetramethylene dications (CH2)42+: are the norbornadiene dication, the pagodane dication, and related systems aromatic? J. Am. Chem. Soc. 1991, 113(10), 3649, doi:10.1021/ja00010a003.