메뉴 건너뛰기




Volumn 16, Issue 19, 2010, Pages 5769-5777

Reaction of 1,1′-divinyl ferrocene with one-electron oxidants: entry into functionalised [4]ferrocenophanes and observation of an Isotope-Dependent chemoselectivity effect

Author keywords

Cyclization; Cyclophanes; Isotope effects; Metallocenes

Indexed keywords

CHEMO-SELECTIVITY; CYCLISATIONS; CYCLOPHANES; FERROCENES; FERROCENOPHANES; GOOD YIELD; ISOTOPE EFFECT; METALLOCENES; ONE-ELECTRON OXIDANTS; REACTION CONDITIONS; VINYL GROUP;

EID: 77952132880     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903478     Document Type: Article
Times cited : (14)

References (46)
  • 2
    • 77952208739 scopus 로고
    • Preparatively useful syntheses of 2 generally begin with ferrocene and involve several steps; bis(acylation), reduction and dehydration, see: M, D. Rausch, A. Siegel, J. Organomet. Chem. 1968, 11, 317324.
    • (1968) J. Organomet. Chem. , vol.11 , pp. 317324
    • Rausch, M.D.1    Siegel, A.2
  • 7
    • 77952219002 scopus 로고    scopus 로고
    • Eds.: R. Gleiter, H. Hopf, Wiley-VCH, Weinheim, Chapter 5
    • a) R. W. Heo, T. R. Lee in Modem Cyclophane Chemistry (Eds.: R. Gleiter, H. Hopf), Wiley-VCH, Weinheim, 2004, Chapter 5, pp. 131-157;
    • (2004) Modem Cyclophane Chemistry , pp. 131-157
    • Heo, R.W.1    Lee, T.R.2
  • 25
    • 77952196455 scopus 로고    scopus 로고
    • A related keto-alcohol ferrocenophane was reported as a minor product from the reaction of l,l'-bis(l-phenylvinyl)ferrocene with molecular oxygen in the presence of a range of Lewis acids; see reference [12b]
    • A related keto-alcohol ferrocenophane was reported as a minor product from the reaction of l,l'-bis(l-phenylvinyl)ferrocene with molecular oxygen in the presence of a range of Lewis acids; see reference [12b].
  • 26
    • 77952180401 scopus 로고    scopus 로고
    • Only 25% of the diol mixture was recovered owing to slow oxidation of the ferrocene to a ferrocenium species as evidenced by the green colouration of the reaction mixture
    • Only 25% of the diol mixture was recovered owing to slow oxidation of the ferrocene to a ferrocenium species as evidenced by the green colouration of the reaction mixture.
  • 36
    • 1642330885 scopus 로고    scopus 로고
    • and references therein
    • H;30), which allows the possibility of using deuterium labelling to modify the chemoselectivity of a reaction; for example, see: E. Vedejs, J. D. Little, J. Org. Chem. 2004, 69, 1794-1799, and references therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 1794-1799
    • Vedejs, E.1    Little, J.D.2
  • 37
    • 77952199460 scopus 로고    scopus 로고
    • We do not discount the possibility that deprotonation (to provide an enolate intermediate) precedes oxidation
    • We do not discount the possibility that deprotonation (to provide an enolate intermediate) precedes oxidation.
  • 38
    • 0001083461 scopus 로고
    • For an example of oxidative cyclisation of δ,εζ- and εζ-unsaturated silyl enol ethers by using copper(II) and cerium(IV) one-electron oxidants, see: B. B. Snider, T. Kwon, J. Org. Chem, 1990, 55, 4786-4788.
    • (1990) J. Org. Chem , vol.55 , pp. 4786-4788
    • Snider, B.B.1    Kwon, T.2
  • 39
    • 0001126489 scopus 로고
    • Silyl enol ethers have also been employed in electrochemical oneelectron oxidation cyclisation reactions: K. D. Moeller, L. V. Tinao, J. Am. Chem. Soc. 1992, 114, 1033-1041.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1033-1041
    • Moeller, K.D.1    Tinao, L.V.2
  • 41
    • 77952168518 scopus 로고    scopus 로고
    • The isolated products and recovered starting material accounted for approximately 40 % mass recovery
    • The isolated products and recovered starting material accounted for approximately 40 % mass recovery.
  • 42
    • 77952158241 scopus 로고    scopus 로고
    • α-Deuteriovinyl ferrocene was prepared in a similar fashion to vinyl ferrocene, see reference [22]
    • α-Deuteriovinyl ferrocene was prepared in a similar fashion to vinyl ferrocene, see reference [22].
  • 45
    • 77952217681 scopus 로고    scopus 로고
    • In this assignment, Cp1. refers to the cyclopentadienyl ring with the α-CH(OH) substituent, Cp2 refers to the cyclopentadienyl ring with the α-keto substituent
    • In this assignment, Cp1. refers to the cyclopentadienyl ring with the α-CH(OH) substituent, Cp2 refers to the cyclopentadienyl ring with the α-keto substituent.
  • 46
    • 77952162289 scopus 로고    scopus 로고
    • CCDC-753882, 753883, 753884, 753885 and 753886 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-753882, 753883, 753884, 753885 and 753886 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.