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Volumn 9, Issue 14, 2003, Pages 3445-3449

Allenes as carbon nucleophiles in intramolecular attack on (π-1,3-diene)-palladium complexes: Evidence for trans carbopalladation of the 1,3-diene

Author keywords

C C coupling; Carbopalladation; Palladium; Reaction mechanisms

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; HYDROCARBONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 0041846416     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305056     Document Type: Article
Times cited : (30)

References (37)
  • 17
    • 0000241359 scopus 로고
    • Attack by an olefin on a (π-olefin)palladium(II) complex has been proposed in palladium-catalyzed Cope rearrangments: L. E. Overman, E. J. Jacobsen, J. Am. Chem. Soc. 1982, 104, 7225.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7225
    • Overman, L.E.1    Jacobsen, E.J.2
  • 18
    • 0034245863 scopus 로고    scopus 로고
    • For recent reviews on allene/palladium chemistry see: a) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; b) R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12
    • (2000) Chem. Rev. , vol.100 , pp. 3067
    • Zimmer, R.1    Dinesh, C.U.2    Nandanan, E.3    Khan, F.A.4
  • 19
    • 0036126987 scopus 로고    scopus 로고
    • For recent reviews on allene/palladium chemistry see: a) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; b) R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 12
    • Bates, R.W.1    Satcharoen, V.2
  • 21
    • 0000263647 scopus 로고
    • J.-E. Bäckvall, R. E. Nordberg, J. Am. Chem. Soc. 1981, 103, 4959; J.-E. Bäckvall, S. E. Byström, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619; J.-E. Bäckvall, R. E. Nordberg, D. Wilhelm, J. Am. Chem. Soc. 1985, 107, 6892.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 4959
    • Bäckvall, J.-E.1    Nordberg, R.E.2
  • 22
    • 26944488411 scopus 로고
    • J.-E. Bäckvall, R. E. Nordberg, J. Am. Chem. Soc. 1981, 103, 4959; J.-E. Bäckvall, S. E. Byström, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619; J.-E. Bäckvall, R. E. Nordberg, D. Wilhelm, J. Am. Chem. Soc. 1985, 107, 6892.
    • (1984) J. Org. Chem. , vol.49 , pp. 4619
    • Bäckvall, J.-E.1    Byström, S.E.2    Nordberg, R.E.3
  • 23
    • 33845378635 scopus 로고
    • J.-E. Bäckvall, R. E. Nordberg, J. Am. Chem. Soc. 1981, 103, 4959; J.-E. Bäckvall, S. E. Byström, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619; J.-E. Bäckvall, R. E. Nordberg, D. Wilhelm, J. Am. Chem. Soc. 1985, 107, 6892.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6892
    • Bäckvall, J.-E.1    Nordberg, R.E.2    Wilhelm, D.3
  • 24
    • 85007645203 scopus 로고    scopus 로고
    • note
    • Other mechanisms involving formation of vinylpalladium in the side chain followed by insertion of the 1,3-diene in the palladium-carbon bond and subsequent acetate attack would also account for the product; see reference [9].
  • 31
    • 85007645198 scopus 로고    scopus 로고
    • note
    • 3).
  • 32
    • 85007641209 scopus 로고    scopus 로고
    • in press
    • In a previous study, the structure 8b was assigned to the product obtained in the palladium-catalyzed (chloride-free) oxidation of 6b in acetic acid. We have later shown that the product from the catalytic reaction has the trans-fused structure; see: J. Löfstedt, K. Närhi, I. Dorange, J.-E. Bäckvall, J. Org. Chem. in press.
    • J. Org. Chem.
    • Löfstedt, J.1    Närhi, K.2    Dorange, I.3    Bäckvall, J.-E.4
  • 33
    • 85007638268 scopus 로고    scopus 로고
    • note
    • Compound 4a has previously been synthesized by another route, and its stereochemistry was fully assigned by analysis of coupling constants; see reference [9].
  • 34
    • 85007634092 scopus 로고    scopus 로고
    • note
    • To confirm the structure of products 8a and 8b, compounds 4a and 4b were converted to 8a and 8b, respectively, under hydrolysis/Mitsunobu conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.