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Volumn 68, Issue 24, 2003, Pages 9340-9347

Secondary Benzylation Using Benzyl Alcohols Catalyzed by Lanthanoid, Scandium, and Hafnium Triflate

Author keywords

[No Author keywords available]

Indexed keywords

EQUILIBRIUM MIXTURES;

EID: 0345686459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034255h     Document Type: Article
Times cited : (232)

References (70)
  • 1
    • 0001586671 scopus 로고
    • Carbon-Carbon u bond formation
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Carbon-Carbon u bond formation. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 293-339.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293-339
    • Olah, G.A.1    Krishnamurti, R.2    Prakash, G.K.S.3
  • 45
    • 0344327788 scopus 로고    scopus 로고
    • note
    • The reaction with a secondary benzylic alcohol, 1-phenylethanol, as an alkylating agent gave styrene as a major product, and several unidentified products were also formed. See ref 10b.
  • 48
    • 0344327786 scopus 로고    scopus 로고
    • note
    • 2a is suitable as a nucleophile for investigating the reactivity of the generated cation, since 2a is selectively alkylated at the 4 position on the naphthalene ring, and unalkylated 2a is recovered without decomposition and is easy to detect by UV absorption. The selective alkylation is due to the electron-withdrawing ester group; therefore, 2a is less nucleophilic than an electron-rich aromatic compound, such as anisole or furan (Chart 1).
  • 52
    • 0002000859 scopus 로고
    • For a review of Lewis acid-promoted enolate alkylations, see: Reetz, M. T. Angew. Chem., Int. Ed. Eng. 1982, 21, 96-108.
    • (1982) Angew. Chem., Int. Ed. Eng. , vol.21 , pp. 96-108
    • Reetz, M.T.1
  • 53
    • 0345190225 scopus 로고    scopus 로고
    • note
    • 3-(2-Naphthyl)-1-phenyl-1-butene.
  • 56
    • 0344327787 scopus 로고    scopus 로고
    • note
    • 4-catalyzed reaction.
  • 57
    • 0345190224 scopus 로고    scopus 로고
    • note
    • endo-Olefin: 1-methyl-3,4-dihydronaphthalene.exo-Olefin: 1-methylene-1,2,3,4-tetrahydro-naphthalene.
  • 67
    • 0345190222 scopus 로고    scopus 로고
    • note
    • The yields of 30 and 31 were calculated based on 20.
  • 68
    • 0345622412 scopus 로고    scopus 로고
    • note
    • The yields were calculated based on 37.
  • 69
    • 0345190223 scopus 로고    scopus 로고
    • note
    • For the reaction with 1, 2-vinylnaphthalene was formed, and for the reaction with 4a, styrene was formed. The structures of the byproducts derived from these olefins are shown in Figure 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.