Regiochemistry of Azide Additions to [70]Fullerene

作者: Berthold Nuber , Andreas Hirsch

DOI: 10.1080/10641229608003012

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摘要: Abstract In this paper we report for the first time on reaction of C70 with alkyl azides and show that [3+2]-cycloaddition occurs preferably at bond 7 followed by 5 to give two regioisomeric A/B-triazolines one C/C-triazoline Thermal extrusion N2 from these triazolines leads open [5,6]-bridged iminofullerenes as A/A- B/C-isomers well ring closed [6,6]-bridged analogues A/B- C/C-isomers. These results are in line corresponding thermal diazomethane.

参考文章(14)
Andreas Hirsch, The chemistry of the fullerenes ,(1994)
Heinrich R. Karfunkel, Andreas Hirsch, Produktvoraussagen bei nucleophilen Additionen an C70 Angewandte Chemie. ,vol. 104, pp. 1529- 1531 ,(1992) , 10.1002/ANGE.19921041128
Alan L. Balch, Vincent J. Catalano, Joong W. Lee, Marilyn M. Olmstead, Sean R. Parkin, (.eta.2-C70)Ir(CO)Cl(PPh3)2: the synthesis and structure of an iridium organometallic derivative of a higher fullerene Journal of the American Chemical Society. ,vol. 113, pp. 8953- 8955 ,(1991) , 10.1021/JA00023A057
Andreas Hirsch, Thomas Grösser, Andreas Skiebe, Antonio Soi, Synthesis of Isomerically Pure Organodihydrofullerenes Chemische Berichte. ,vol. 126, pp. 1061- 1067 ,(1993) , 10.1002/CBER.19931260428
Thomas Grösser, Maurizio Prato, Vittorio Lucchini, Andreas Hirsch, Fred Wudl, Ringexpansion des Fullerengerüstes durch hochregioselektive Bildung von Diazafulleroiden Angewandte Chemie. ,vol. 107, pp. 1462- 1464 ,(1995) , 10.1002/ANGE.19951071218
Axel Meyer, Michael A. Solow, Joel M. Hawkins, Osmylation of C70: reactivity versus local curvature of the fullerene spheroid Journal of the American Chemical Society. ,vol. 115, pp. 7499- 7500 ,(1993) , 10.1021/JA00069A058
Craig C. Henderson, Celeste McMichael Rohlfing, Paul A. Cahill, Theoretical studies of selected C60H2 and C70H2 isomers Chemical Physics Letters. ,vol. 213, pp. 383- 388 ,(1993) , 10.1016/0009-2614(93)85150-M
M. Prato, Q. Chan Li, F. Wudl, V. Lucchini, Addition of azides to fullerene C60: synthesis of azafulleroids Journal of the American Chemical Society. ,vol. 115, pp. 1148- 1150 ,(1993) , 10.1021/JA00056A049
Fran�ois Diederich, Lyle Isaacs, Douglas Philp, Syntheses, structures, and properties of methanofullerenes Chemical Society Reviews. ,vol. 23, pp. 243- 255 ,(1994) , 10.1039/CS9942300243
Iris Lamparth, Berthold Nuber, Georg Schick, Andreas Skiebe, Thomas Grösser, Andreas Hirsch, C59N+ und C69N+: isoelektronische Hetero-Analoga von C60 und C70 Angewandte Chemie. ,vol. 107, pp. 2473- 2476 ,(1995) , 10.1002/ANGE.19951072035