Download PDF
Synthesis 2004(18): 2962-2964  
DOI: 10.1055/s-2004-834891
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Carbon-Carbon Bond Cleavage of an Open-Cage Diketone Derivative of [60]Fullerene by Reaction with Aromatic Hydrazones

Sho-ichi Iwamatsu*a, Toshiki Kuwayamaa, Kaoru Kobayashib, Shigeru Nagaseb, Shizuaki Murata*a,c
a Graduate School of Environmental Studies, Nagoya University, Nagoya, 464-8601, Japan
Fax: +81(52)7894765; e-Mail: iwmt@urban.env.nagoya-u.ac.jp;
b Institute for Molecular Science, Okazaki, 444-8585, Japan
c CREST, Japan Science and Technology Agency (JST), Japan
Further Information

Publication History

Received 3 August 2004
Publication Date:
22 October 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

The addition reaction of aromatic hydrazone to the diketone derivative of C60 occurred with a regioselective C-C bond scission to afford a ring-expanded product having a 16-membered ring orifice.

Key words

fullerenes - cleavage - ring expansion - hydrazones

    References

  • 1a Rubin Y. Top. Curr. Chem.  1999,  199:  67 
    CrossrefGoogle Scholar
  • 1b Rubin Y. Diederich F. In Stimulating Concepts in Chemistry   Vögtle F. Stoddart JF. Shibasaki M. Wiley-VCH; Weinheim: 2000.  p.163 
    CrossrefGoogle Scholar
  • 1c Nierengarten J.-F. Angew. Chem. Int. Ed.  2001,  40:  2973 
    CrossrefGoogle Scholar
  • 2a Rubin Y. Jarrosson T. Wang G.-W. Bartberger MD. Houk KN. Schick G. Saunders M. Cross RJ. Angew. Chem. Int. Ed.  2001,  40:  1543 
    CrossrefGoogle Scholar
  • 2b Irle S. Rubin Y. Morokuma K. J. Phys. Chem. A  2002,  106:  680 
    CrossrefGoogle Scholar
  • 3a Murata Y. Murata M. Komatsu K. Chem. Eur. J.  2003,  9:  1600 
    CrossrefGoogle Scholar
  • 3b Murata Y. Murata M. Komatsu K. J. Am. Chem. Soc.  2003,  125:  7125 
    CrossrefGoogle Scholar
  • 3c Carravetta M. Murata Y. Murata M. Heinmaa I. Stern R. Tontcheva A. Samoson A. Rubin Y. Komatsu K. Levitt MH. J. Am. Chem. Soc.  2004,  126:  4092 
    CrossrefGoogle Scholar
  • 3d Yoshimoto S. Tsutsumi E. Honda Y. Murata Y. Murata M. Komatsu K. Ito O. Itaya K. Angew. Chem. Int. Ed.  2004,  43:  3044 
    CrossrefGoogle Scholar
  • 3e Vougioukalakis GC. Prassides K. Orfanopoulos M. Org. Lett.  2004,  6:  1245 
    CrossrefGoogle Scholar
  • 4a Inoue H. Yamaguchi H. Iwamatsu S.-i. Uozaki T. Suzuki T. Akasaka T. Nagase S. Murata S. Tetrahedron Lett.  2001,  42:  895 
    CrossrefGoogle Scholar
  • 4b Murata Y. Komatsu K. Chem. Lett.  2001,  896 
    CrossrefGoogle Scholar
  • 4c Murata Y. Murata M. Komatsu K. J. Org. Chem.  2001,  66:  8187 
    CrossrefGoogle Scholar
  • 5a Iwamatsu S.-i. Ono F. Murata S. Chem. Commun.  2003,  1268 
    CrossrefGoogle Scholar
  • 5b Iwamatsu S.-i. Ono F. Murata S. Chem. Lett.  2003,  32:  614 
    CrossrefGoogle Scholar
  • 5c Vougioukalakis GC. Prassides K. Campanera JM. Heggie MI. Orfanopoulos M. J. Org. Chem.  2004,  69:  4524 
    CrossrefGoogle Scholar
  • 6a Iwamatsu S.-i. Uozaki T. Kobayashi K. Re S. Nagase S. Murata S. J. Am. Chem. Soc.  2004,  126:  2668 
    CrossrefGoogle Scholar
  • 6b Iwamatsu S.-i. Murata S. Tetrahedron Lett.  2004,  45:  6391 
    CrossrefGoogle Scholar
  • 7a Kuder JE. Tetrahedron  1981,  28:  1973 
    CrossrefGoogle Scholar
  • 7b Soliman FM. Yakout El-SM. Said MM. Bull. Chem. Soc. Jpn.  1994,  67:  2162 
    CrossrefGoogle Scholar
  • 8 Frisch MJ. Trucks GW. Schlegel HB. Scuseria GE. Robb MA. Cheeseman JR. Montgomery JA. Vreven TJr. Kudin KN. Burant JC. Millam JM. Iyengar SS. Tomasi J. Barone V. Mennucci B. Cossi M. Scalmani G. Rega N. Petersson GA. Nakatsuji H. Hada M. Ehara M. Toyota K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Klene M. Li X. Knox JE. Hratchian HP. Cross JB. Adamo C. Jaramillo J. Gomperts R. Stratmann RE. Yazyev O. Austin AJ. Cammi R. Pomelli C. Ochterski JW. Ayala PY. Morokuma K. Voth GA. Salvador P. Dannenberg JJ. Zakrzewski VG. Dapprich S. Daniels AD. Strain MC. Farkas O. Malick DK. Rabuck AD. Raghavachari K. Foresman JB. Ortiz JV. Cui Q. Baboul AG. Clifford S. Cioslowski J. Stefanov BB. Liu G. Liashenko A. Piskorz P. Komaromi I. Martin RL. Fox DJ. Keith T. Al-Laham MA. Peng CY. Nanayakkara A. Challacombe M. Gill PMW. Johnson B. Chen W. Wong MW. Gonzalez C. Pople JA. Gaussian 03 Revision B.02   Gaussian Inc.; Pittsburgh PA: 2003. 
    Google Scholar