Ring Expansion of the Fullerene Core by Highly Regioselective Formation of Diazafulleroids†
Thomas Grösser
Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
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Prof. Dr. Maurizio Prato
Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
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Prof. Dr. Vittorio Lucchini
Dipartimento di Scienze Ambientali, Venezia (Italy)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
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Prof. Dr. Andreas Hirsch
Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
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Prof. Dr. Fred Wudl
Institute for Polymers and Organic Solids, Santa Barbara (USA)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
Search for more papers by this authorThomas Grösser
Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Search for more papers by this authorCorresponding Author
Prof. Dr. Maurizio Prato
Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Vittorio Lucchini
Dipartimento di Scienze Ambientali, Venezia (Italy)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Andreas Hirsch
Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Fred Wudl
Institute for Polymers and Organic Solids, Santa Barbara (USA)
Maurizio Prato, Dipartimento di Scienze Farmaceutiche, Trieste (Italy)
Vittorio Lucchini, Dipartimento di Scienze Ambientali, Venezia (Italy)
Andreas Hirsch, Institut für Organische Chemie, Richard-Willstätter-Allee 2, D-76131 Karlsruhe (Germany), Telefax: Int. code + (721) 698-305
Fred Wudl, Institute for Polymers and Organic Solids, Santa Barbara (USA)
Search for more papers by this authorThis work was supported by the Deutsche Forschungsgemeinschaft (DFG), the Bundesministerium für Forschung und Technologie (BMFT), and Hoechst AG. M. P. thanks the Consiglio Nazionale delle Richerche for a travel grant. F. W. wishes to thank National Science Foundation for support (grant DMR91-22536).
Graphical Abstract
Fullerenes with enlarged openings such as diazafulleroid 1 are obtained by twofold addition of azides to C60. Even after cleavage of the two 5–6 bonds and introduction of the imino bridges, the π-electron system of C60 remains intact. Compound 1 contains three seven-membered rings and one eleven-membered ring, and may hold the key to the synthesis of endohedral fullerenes under mild conditions.
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