β-Hydroxy nitrile and β-hydroxy oxime derivatives of [60]fullerene by nucleophilic ring cleavage of fulleroisoxazoline and - Isoxazolidine in the presence of methanol

Synlett

Volumn , Issue 3, 2000, Pages 361-362

  Yashiro, A ^a   Nishida, Y ^a   Kobayashi, K ^a   Ohno, M ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b TOYOTA TECHNOLOGICAL INSTITUTE   (Japan)

Author keywords

hydroxy nitrile; hydroxy oxime; 60 fullerene; Nitrone; Ring cleavage

Indexed keywords

FULLERENE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; METHANOL; NITRILE; OXIME DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; LOW TEMPERATURE PROCEDURES; REACTION ANALYSIS; SYNTHESIS;

EID: 0034053042     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

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2. For reviews, see: Averdung, J.; Torres-Garcia, G.; Luftmann, H.; Schlachter, I.; Mattey, J. Fullerene Sci. Tech. 1996, 4, 633. Sliwa, W. Fullerene Sci. Tech. 1997, 5, 1133. For our own works, see: Ohno, M.; Sato, H.; Eguchi, S. Synlett 1999, 207 and refs cited therein.
3. For reviews, see: Averdung, J.; Torres-Garcia, G.; Luftmann, H.; Schlachter, I.; Mattey, J. Fullerene Sci. Tech. 1996, 4, 633. Sliwa, W. Fullerene Sci. Tech. 1997, 5, 1133. For our own works, see: Ohno, M.; Sato, H.; Eguchi, S. Synlett 1999, 207 and refs cited therein.
4. For reviews, see: Averdung, J.; Torres-Garcia, G.; Luftmann, H.; Schlachter, I.; Mattey, J. Fullerene Sci. Tech. 1996, 4, 633. Sliwa, W. Fullerene Sci. Tech. 1997, 5, 1133. For our own works, see: Ohno, M.; Sato, H.; Eguchi, S. Synlett 1999, 207 and refs cited therein.
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6. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371. Fukuzumi, S.; Nakanishi, I.; Maruta, J.; Yorisue, T.; Suenobu, T.; Itoh, S.; Arakawa, R., Kadish, K. M. J. Am. Chem. Soc. 1998, 120, 6673. Kitagawa, T.; Sakamoto, H.; Takeuchi, K. J. Am. Chem. Soc. 1999, 121, 4298.
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10. Banks, M. R.; Cadgan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. R., Taylor, A. T. Tetrahedron Lett. 1994, 35, 9067. Zhang, X.; Romero, A.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 11024. Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 4271.
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14. Even simple heating of free alcohol 7 returned to pristine [60]fullerene, presumably via an analogous process.
15. LDA is documented to be compatible with the known baselability of [60]fullerene core; Benito, A. M.; Darwish, A. D.; Kroto, H. W.; Meidine, M. F.; Taylor, R.; Walton, D. R. M. Tetrahedron Lett. 1996, 37, 1085.
16. Irmgartinger, H.; Weber, A. Tetrahedron Lett. 1997, 38, 2075.
17. 2) δ 62.69, 90.56, 126.88, 139.46, 139.73, 143.38, 143.49, 144.55, 144.88, 145.05, 145.33, 145.59, 146.10, 146.11, 146.16, 146.28, 147.30, 147.38, 147.72, 147.93, 148.63, 148.76, 148.85, 149.40, 149.58, 149.63, 149.73, 149.93, 150.01, 150.02, 151.28, 151.47, 151.77.
18. Yashiro, A.; Nishida, Y.; Ohno, M.; Eguchi, S.; Kobayashi, K. Tetrahedron Lett. 1998, 39, 9031.
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20. Ohno, M.; Yashiro, A.; Tsunenishi, Y.; Eguchi, S. Chem. Commun. 1999, 827. As a typical case, the spectral data for 8b are given in this report.