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Volumn 66, Issue 3, 1998, Pages 881-884

Highly regioselective thioselenation of acetylenes by using a (PhS)2-(phse)2 binary system

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EID: 85113720008     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo971652h     Document Type: Article
Times cited : (81)

References (32)
  • 3
    • 33947335344 scopus 로고
    • For the addition of disulfides to acetylenes, see: (a) Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837.
    • (1967) J. Org. Chem. , vol.32 , pp. 3837
    • Heiba, E.I.1    Dessau, R.M.2
  • 4
    • 33845278103 scopus 로고
    • For the addition of diselenides to acetylenes, see: (b) Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533.
    • (1988) J. Org. Chem. , vol.53 , pp. 2533
    • Back, T.G.1    Krishna, M.V.2
  • 9
    • 0010158192 scopus 로고
    • Sulfur, Silicon
    • Ogawa, A.; Sonoda, N. Phosphorus, Sulfur, Silicon, 1994, 95-96, 331.
    • (1994) Phosphorus , vol.95-96 , pp. 331
    • Ogawa, A.1    Sonoda, N.2
  • 10
    • 0001086740 scopus 로고
    • The rate constants for the SH2 reaction of 5-hexenyl radical with (PhS)2 and (PhSe)2 are determined to be 7.6 × 104 M-1 s-1 and 1.2 × 107 M-1 s-1, respectively.
    • 1, respectively. See: (a) Russell, G. A.; Tashtoush, H. J. Am. Chem. Soc. 1983, 105, 1398.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1398
    • Russell, G.A.1    Tashtoush, H.2
  • 13
    • 0020704104 scopus 로고
    • the case of styrene, for example, the addition rate constants of PhS• and PhSe• are estimated to be 5.1 × 107 M-1 s-1 and 2.2 × 106 M-1 s-1, respectively
    • 1, respectively. See: (a) Ito, O. J. Am. Chem. Soc. 1983, 105, 850.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 850
    • Ito, O.1
  • 24
    • 0000315424 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Curran, D. P. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 779.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779
    • Curran, D.P.1
  • 26
    • 85113755340 scopus 로고    scopus 로고
    • The thioselenation of enynes was accompanied by the formation of acyclic thioselenation products: CH2dCHCH2XCH2C(SePh)dCHSPh, X) C(CO2Et)2: 7% (E/Z ) 79/21); X) O: 11% (E/Z ) 79/21
    • The thioselenation of enynes was accompanied by the formation of acyclic thioselenation products: CH2dCHCH2XCH2C(SePh)dCHSPh, X) C(CO2Et)2: 7% (E/Z ) 79/21); X) O: 11% (E/Z ) 79/21).
  • 32
    • 85113806278 scopus 로고    scopus 로고
    • was irradiated with a tungsten lamp, PhSSePh was formed in situ (the ratio of (PhS)2/ (PhSe)2/PhSSePh was ca. 1/1/1.4 during the thioselenation of olefins
    • When a mixture of (PhS)2 and (PhSe)2 (1:1) was irradiated with a tungsten lamp, PhSSePh was formed in situ (the ratio of (PhS)2/ (PhSe)2/PhSSePh was ca. 1/1/1.4 during the thioselenation of olefins).
    • When a Mixture of (PhS)2 and (PhSe)2 (1:1)


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