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Volumn 124, Issue 41, 2002, Pages 12335-12342

Theoretical study of silylene substituent effects on the abstraction reactions with oxirane and thiirane

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTION REACTIONS;

EID: 0037120886     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020515l     Document Type: Article
Times cited : (21)

References (65)
  • 7
    • 0001979412 scopus 로고
    • Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York
    • (a) Gaspar, P. P. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2, pp 335-385.
    • (1981) Reactive Intermediates , vol.2 , pp. 335-385
    • Gaspar, P.P.1
  • 8
    • 0001127595 scopus 로고
    • Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York
    • (b) Gaspar, P. P. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1985; Vol. 3, pp 333-427.
    • (1985) Reactive Intermediates , vol.3 , pp. 333-427
    • Gaspar, P.P.1
  • 35
    • 2142748260 scopus 로고    scopus 로고
    • note
    • 9a it was found that singlet carbenes are capable of abstracting an oxygen atom from oxirane as well as a sulfur atom from thiirane. Several qualitative conclusions concerning the oxirane deoxygenation were obtained. (1) The magnitudes of the rate constants for oxygen atom transfer are dependent on the philicity of the carbene intermediate. (2) Trends in the kinetic data suggest that oxygen atom transfer occurs by a concerted mechanism through ylide-like transition states. (3) Ylides formed by the attack of carbenes on heteroatom donors were not actually observed for any of the heteroatom transfer reactions. (4) Absolute rate constants for the heteroatom transfer show that oxirane deoxygenation is a facile process.
  • 44
    • 0001610260 scopus 로고    scopus 로고
    • (c) Jursic, B. THEOCHEM 1998, 425, 193.
    • (1998) THEOCHEM , vol.425 , pp. 193
    • Jursic, B.1
  • 45
    • 0001504314 scopus 로고    scopus 로고
    • (d) Jursic, B. THEOCHEM 1998, 452, 145.
    • (1998) THEOCHEM , vol.452 , pp. 145
    • Jursic, B.1
  • 61
    • 2142685824 scopus 로고
    • Academic Press: New York
    • Johnson, A. W. Ylide Chemistty; Academic Press: New York, 1966; p 251.
    • (1966) Ylide Chemistty , pp. 251
    • Johnson, A.W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.