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Volumn 38, Issue 6, 2009, Pages 628-629

Dual functionalization of allene: facile construction of heteropolycycles mediated by Brønsted acid

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EID: 67650505545     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.628     Document Type: Article
Times cited : (10)

References (30)
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  • 12
    • 0038467825 scopus 로고    scopus 로고
    • For hydrofunctionalization of allene, see: a
    • For hydrofunctionalization of allene, see: a) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
    • (2002) Org. Lett , vol.4 , pp. 2989
    • Ma, S.1    Gao, W.2
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    • Akiyama, T.1
  • 25
    • 67650491924 scopus 로고    scopus 로고
    • Crystallographic data reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no
    • Crystallographic data reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-726048.
    • , vol.CCDC-726048
  • 26
    • 0025305009 scopus 로고    scopus 로고
    • In a formal sense, the formation of allylic carbocation intermediate by protonation of the center carbon overwhelms that of vinyl cation. However, kinetically favored protonation furnishes the vinyl cation intermediate. This result could be explained by stereoelectronic factors. Because the allene structure is nonplanar, an initial protonation of the center carbon leads to a twisted structure that avoids allylic conjugation. See: a K. B. Wiberg, C. M. Breneman, T. J. LePage, J. Am. Chem. Soc. 1990, 112, 61
    • In a formal sense, the formation of allylic carbocation intermediate by protonation of the center carbon overwhelms that of vinyl cation. However, kinetically favored protonation furnishes the vinyl cation intermediate. This result could be explained by stereoelectronic factors. Because the allene structure is nonplanar, an initial protonation of the center carbon leads to a twisted structure that avoids allylic conjugation. See: a) K. B. Wiberg, C. M. Breneman, T. J. LePage, J. Am. Chem. Soc. 1990, 112, 61.
  • 28
    • 67650460053 scopus 로고    scopus 로고
    • Naphthalene 5 was formed by olefin isomerization from intermediate F followed by dehydrative 1, 2-phenyl migration.
    • Naphthalene 5 was formed by olefin isomerization from intermediate F followed by dehydrative 1, 2-phenyl migration.
  • 29
    • 67650476808 scopus 로고    scopus 로고
    • The preparation of corresponding starting materials (8b and 8c) is described in Supporting Information.
    • The preparation of corresponding starting materials (8b and 8c) is described in Supporting Information.
  • 30
    • 67650488703 scopus 로고    scopus 로고
    • Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
    • Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.