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Volumn 65, Issue 52, 2009, Pages 10769-10783

The reaction of biphenyl radical anion and dianion with alkyl fluorides. From ET to SN2 reaction pathways and synthetic applications

Author keywords

Alkyl fluorides; Biphenyl dianion; Biphenyl radical anion; Dearomatization; SN reaction

Indexed keywords

ALKYL GROUP; ANION; BIPHENYL DERIVATIVE; FLUORIDE; LITHIUM DERIVATIVE; METHYL GROUP; RADICAL;

EID: 70449880098     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.027     Document Type: Article
Times cited : (13)

References (46)
  • 2
    • 23944482383 scopus 로고    scopus 로고
    • This has resulted in numerous synthetic applications:. Rappoport Z., and Marek I. (Eds), Wiley, Chichester, UK Part 2
    • This has resulted in numerous synthetic applications:. Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), Wiley, Chichester, UK 657-747 Part 2
    • (2004) The Chemistry of Organolithium Compounds , vol.1 , pp. 657-747
    • Yus, M.1
  • 4
    • 0003998388 scopus 로고    scopus 로고
    • 85th ed, Lide, Dr, Ed, CRC: Boca Raton, FL
    • CRC Handbook of Chemistry and Physics, 85th ed.; Lide, Dr., Ed.; CRC: Boca Raton, FL, 2004; pp 8-33.
    • (2004) CRC Handbook of Chemistry and Physics , pp. 8-33
  • 5
    • 70449991021 scopus 로고    scopus 로고
    • For reduction potentials of Li
    • For reduction potentials of Li
  • 8
    • 70449859661 scopus 로고    scopus 로고
    • note
    • 2: See reference 1.
  • 13
    • 33746280377 scopus 로고
    • Chem. Abstr. 92 (1980) 110107
    • (1980) Chem. Abstr. , vol.92 , pp. 110107
  • 18
    • 0038245415 scopus 로고
    • 5 the stabilization due to ion-pairing equilibria of the dissolved species, the solvent, the concentration and the temperature, all of which can be further complicated by the appearance of new phases. Disproportionation equilibria are profoundly affected by the medium (e.g., by small changes in the solvent; ), and the complex kinetics inherent to heterogeneous ET processes on metal surfaces along with the intrinsic high reactivity of the species involved makes difficult the determination of the actual composition of the reaction media.
    • 5 the stabilization due to ion-pairing equilibria of the dissolved species, the solvent, the concentration and the temperature, all of which can be further complicated by the appearance of new phases. Disproportionation equilibria are profoundly affected by the medium (e.g., by small changes in the solvent;. Levin G., Holloway B.E., and Szwarc M. J. Am. Chem. Soc. 98 (1976) 5706-5709 ), and the complex kinetics inherent to heterogeneous ET processes on metal surfaces along with the intrinsic high reactivity of the species involved makes difficult the determination of the actual composition of the reaction media. For all this, in addition to spectroscopic claims, we included available electrochemical data on the generation of biphenyl dianion, so the arguments concerning the generation and stability of some of these highly reduced species do not rest exclusively on spectroscopic grounds
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 5706-5709
    • Levin, G.1    Holloway, B.E.2    Szwarc, M.3
  • 38
    • 70449903431 scopus 로고    scopus 로고
    • note
    • The reaction has an identical outcome in the case of secondary alkyl fluorides, affording products 5a-e, while the regiochemistry of alkylation switches to 4-alkyl-3-substituted-1,4-dihydrobiphenyls (6a-c) for tertiary alkyl fluorides, which are obtained in lower yields. As a whole, it should be emphasized that using this methodology biphenyl is partially dearomatized and doubly derivatized in a one pot reaction.
  • 42
    • 47249106330 scopus 로고    scopus 로고
    • George Thieme Verlag, Stuttgart Vol. 34, pp 71-148
    • Dax K. Science of Synthesis (2006), George Thieme Verlag, Stuttgart Vol. 34, pp 71-148
    • (2006) Science of Synthesis
    • Dax, K.1
  • 45
    • 70450046904 scopus 로고
    • Chem. Abstr. 95 (1981) 186706
    • (1981) Chem. Abstr. , vol.95 , pp. 186706


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.