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Volumn 74, Issue 4, 2009, Pages 1480-1487

H-bond-assisted regioselective (cis-1) intramolecular nucleophilic addition of the hydroxyl group to [60]fullerene

Author keywords

[No Author keywords available]

Indexed keywords

[60] FULLERENES; DENSITY FUNCTIONAL; DOUBLE BONDS; HYDROXY GROUPS; HYDROXYL GROUPS; HYDROXYLIC GROUPS; INTRAMOLECULAR CYCLIZATION; METHYL GROUPS; MOLECULAR GEOMETRIES; NITROGEN ATOMS; NUCLEOPHILIC ADDITIONS; ONE-STEP REACTIONS; ONIOM APPROACHES; ORGANOFULLERENE; PYRROLIDINE RINGS; REFLUXING; REGIO-SELECTIVE; SARCOSINE; THEORETICAL CALCULATIONS;

EID: 64349095267     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802152x     Document Type: Article
Times cited : (35)

References (64)
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    • For some recent books, see: (a) Hirsch, A. The Chemistry of Fullerenes; Wiley-VCH:, Weinheim, Germany, 2005.
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    • The reaction of 1 with 2b afforded, in addition to the expected compound 3b in 25% yield, a minor compound 4 (8% yield), which was identified as the parent unsubstituted pyrrolidino[3,4:1,2][60]fullerene. The formation of this compound in which the aryl group on the pyrrolidine ring has been lost is not clear yet. However, some related cases have been reported in the literature. See: (a) Zhou, D.; Tan, H.; Luo, C.; Gan, L.; Huang, C.; Pan, J.; Lu, M.; Wu, Y. Tetrahedron Lett. 1995, 36, 9169-9172.
    • The reaction of 1 with 2b afforded, in addition to the expected compound 3b in 25% yield, a minor compound 4 (8% yield), which was identified as the parent unsubstituted pyrrolidino[3,4:1,2][60]fullerene. The formation of this compound in which the aryl group on the pyrrolidine ring has been lost is not clear yet. However, some related cases have been reported in the literature. See: (a) Zhou, D.; Tan, H.; Luo, C.; Gan, L.; Huang, C.; Pan, J.; Lu, M.; Wu, Y. Tetrahedron Lett. 1995, 36, 9169-9172.
  • 29
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    • Although the presence of two electron-releasing methoxy groups in the benzene ring could have an impact on the acidic character of the OH group, their relative meta position prevents the conjugative effect. A weak inductive effect cannot be, however, ruled out
    • Although the presence of two electron-releasing methoxy groups in the benzene ring could have an impact on the acidic character of the OH group, their relative meta position prevents the conjugative effect. A weak inductive effect cannot be, however, ruled out.
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    • For a systematic and simple site labelling system to indicate the relative positional relationships of addends in fullerene derivatives, see: Hirsch, A, Lamparth, I, Karfunkel, H. R. Ansew. Chem, Int. Ed. 1994, 33, 437-438
    • For a systematic and simple site labelling system to indicate the relative positional relationships of addends in fullerene derivatives, see: Hirsch, A.; Lamparth, I.; Karfunkel, H. R. Ansew. Chem., Int. Ed. 1994, 33, 437-438.
  • 37
    • 64349092755 scopus 로고    scopus 로고
    • We want to thank to one of the referees for this interesting suggestion, which has allowed a better understanding of this cyclization process
    • We want to thank to one of the referees for this interesting suggestion, which has allowed a better understanding of this cyclization process.
  • 38
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    • 1H NMR spectroscopy.
    • 1H NMR spectroscopy.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.