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Volumn 44, Issue 4, 1996, Pages 703-708

α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms

Author keywords

hypofluorous acid; molecular fluorine; non Pummerer type reaction; fluorination; fluorosulfone

Indexed keywords

ALPHA FLUOROSULFONE; FLUORINE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0029870277     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.703     Document Type: Article
Times cited : (25)

References (42)
  • 16
    • 9344271792 scopus 로고    scopus 로고
    • note
    • In most cases, fluorination by molecular fluorine has been carried out using fluorotrichloromethane (expensive) as the solvent and hence, the method as a whole is considered uneconomical. However, as stated below, solvent was not indispensable for this kind of fluorination reaction.
  • 21
    • 0000871996 scopus 로고
    • Since 6a belongs to the class of so-called hypervalent molecules (molecules with more than an octet of electrons around the central atom), one should consider the participation of electron-rich three-center bonding. The results suggests that the best stabilization will arise when the terminal atoms of the trigonal bipyramidal structure are electron-negative ones. Martin J. C., Science, 221, 509 (1983); Albright T. A., Burdett J. K., Whangbo, M-H., "Orbital Interactions in Chemistry," John Wiley & Sons, New York, 1985, pp. 258-276.
    • (1983) Science , vol.221 , pp. 509
    • Martin, J.C.1
  • 22
    • 0003947806 scopus 로고
    • John Wiley & Sons, New York
    • Since 6a belongs to the class of so-called hypervalent molecules (molecules with more than an octet of electrons around the central atom), one should consider the participation of electron-rich three-center bonding. The results suggests that the best stabilization will arise when the terminal atoms of the trigonal bipyramidal structure are electron-negative ones. Martin J. C., Science, 221, 509 (1983); Albright T. A., Burdett J. K., Whangbo, M-H., "Orbital Interactions in Chemistry," John Wiley & Sons, New York, 1985, pp. 258-276.
    • (1985) Orbital Interactions in Chemistry , pp. 258-276
    • Albright, T.A.1    Burdett, J.K.2    Whangbo3    M-H4
  • 27
    • 9344242647 scopus 로고    scopus 로고
    • note
    • 2].
  • 29
    • 9344228717 scopus 로고
    • 2O/ AcONa was reported to give the α-acetoxylated sulfides in good yields. High temperature as well as the presence of base (AcONa) might be necessary for the required deprotonation. See, Masuda T., Numata T., Furukawa N., Oae S., J. Chem. Soc., Perkin Trans. 2, 1979, 1302.
    • (1302) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1979
    • Masuda, T.1    Numata, T.2    Furukawa, N.3    Oae, S.4
  • 30
    • 9344263701 scopus 로고    scopus 로고
    • note
    • 2: the precursor of 17].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.