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Volumn 288, Issue 5467, 2000, Pages 834-836

Stable versions of transient push-pull carbenes: Extending lifetimes from nanoseconds to weeks

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE;

EID: 0034607853     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.288.5467.834     Document Type: Article
Times cited : (132)

References (36)
  • 3
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    • W. Kirmse, Ed., Carbene Chemistry (Academic Press, New York, ed. 2, 1971).
    • (1971) Carbene Chemistry , vol.2
    • Kirmse, W.1
  • 4
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    • Wiley, New York
    • M. Jones and R. A. Moss, Eds., Carbenes, vol. II (Wiley, New York, 1975).
    • (1975) Carbenes , vol.2
    • Jones, M.1    Moss, R.A.2
  • 17
    • 0343955844 scopus 로고
    • thesis, University of Pennsylvania, Philadelphia
    • J. E. O'Gara, thesis, University of Pennsylvania, Philadelphia, (1992).
    • (1992)
    • O'Gara, J.E.1
  • 18
    • 0343955846 scopus 로고    scopus 로고
    • note
    • Selected spectroscopic data for derivatives 2, 3, 4, and 10 are available at Science Online (33).
  • 19
    • 0343520051 scopus 로고    scopus 로고
    • note
    • The single-crystal x-ray diffraction studies for 2 and 6 will be published elsewhere.
  • 22
    • 11944273856 scopus 로고
    • 1,2-F migration leading to the corresponding alkene has been observed for transient singlet halogeno(trifluoromethyl)carbenes [J. E. O'Gara and W. P. Dailey, J. Am. Chem. Soc. 114, 3581 (1992)]; moreover, C-fluorinated phosphorus ylides are known to rearrange into the corresponding phosphacumulene by 1,2-F migration from carbon to phosphorus [ K. G. Sharp and I. Schwager, Inorg. Chem. 15, 1697 (1976)].
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3581
    • O'Gara, J.E.1    Dailey, W.P.2
  • 23
    • 0039105849 scopus 로고
    • 1,2-F migration leading to the corresponding alkene has been observed for transient singlet halogeno(trifluoromethyl)carbenes [J. E. O'Gara and W. P. Dailey, J. Am. Chem. Soc. 114, 3581 (1992)]; moreover, C-fluorinated phosphorus ylides are known to rearrange into the corresponding phosphacumulene by 1,2-F migration from carbon to phosphorus [ K. G. Sharp and I. Schwager, Inorg. Chem. 15, 1697 (1976)].
    • (1976) Inorg. Chem. , vol.15 , pp. 1697
    • Sharp, K.G.1    Schwager, I.2
  • 25
    • 0040289842 scopus 로고
    • Stuttgart, New York
    • The reaction of transient dihalogenocarbenes with phosphines is a preparative method for C-dihalogeno phosphorus ylides [H. J. Bestmann and R. Zimmermann, Methoden der Organischen Chemie Organischen Chemie (Houben-Weyl), vol. E1 (Stuttgart, New York, 1982), pp. 616-618; A. W. Johnson et al., in Ylides and Imines of Phosphorus, A. W. Johnson, Ed. (Wiley-Interscience, New York, 1993), pp. 115-116].
    • (1982) Methoden der Organischen Chemie Organischen Chemie (Houben-Weyl) , vol.E1 , pp. 616-618
    • Bestmann, H.J.1    Zimmermann, R.2
  • 26
    • 0039697995 scopus 로고
    • A. W. Johnson, Ed. Wiley-Interscience, New York
    • The reaction of transient dihalogenocarbenes with phosphines is a preparative method for C-dihalogeno phosphorus ylides [H. J. Bestmann and R. Zimmermann, Methoden der Organischen Chemie Organischen Chemie (Houben-Weyl), vol. E1 (Stuttgart, New York, 1982), pp. 616-618; A. W. Johnson et al., in Ylides and Imines of Phosphorus, A. W. Johnson, Ed. (Wiley-Interscience, New York, 1993), pp. 115-116].
    • (1993) Ylides and Imines of Phosphorus , pp. 115-116
    • Johnson, A.W.1
  • 31
    • 0343520049 scopus 로고    scopus 로고
    • note
    • Various transient trifluoromethylcarbenes are known to insert into silicon-hydrogen bonds (16).
  • 33
    • 0343955843 scopus 로고    scopus 로고
    • note
    • Crystal data for 10 are available at Science Online (33).
  • 34
    • 0343520048 scopus 로고    scopus 로고
    • note
    • 13C NMR signals corresponding to C3, C5, and C7, which appear at high field, whereas those for C4 and C6 are more deshielded (18).
  • 35
    • 0343520047 scopus 로고    scopus 로고
    • For supplementary data, see www.sciencemag.org/ feature/data/1048933.shl.
  • 36
    • 0343083903 scopus 로고    scopus 로고
    • note
    • We are grateful to the CNRS for financial support of this work.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.