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Volumn 127, Issue 41, 2005, Pages 14239-14249

Alkene cis-dihydroxylation by [(Me3tacn)(CF3CO 2)RuVIO2]CIO4 (Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane): Structural characterization of [3 + 2] cycloadducts and kinetic studies

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALCOHOLS; OXIDATION; RATE CONSTANTS; REACTION KINETICS; STYRENE;

EID: 26844562589     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0528230     Document Type: Article
Times cited : (98)

References (111)
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    • (d) Gao, Y. In Encyclopedia of Reagents for Organic Synthesis: Paquette, L. A., Editor-in-Chief; Wiley: New York, 1995: Vol. 6, p 3801.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.6 , pp. 3801
    • Gao, Y.1
  • 20
    • 0003579939 scopus 로고
    • Paquette, L. A., Editor-in Chief; Wiley: New York
    • (b) Lee, D. G. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Editor-in Chief; Wiley: New York, 1995; Vol. 6, p 4274.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.6 , pp. 4274
    • Lee, D.G.1
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    • Abel, E. W., Stone, F. G. A., Wilkinson, G. W., Eds.; Pergamon: Oxford
    • (c) Murahashi, S.-I.; Naota, T. In Comprehensive Organometallic Chemistry II. Vol. 12; Abel, E. W., Stone, F. G. A., Wilkinson, G. W., Eds.; Pergamon: Oxford. 1995; p 1177.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1177
    • Murahashi, S.-I.1    Naota, T.2
  • 56
    • 0000036757 scopus 로고
    • Trost, B. M., Fleming, I., Ley, S. V., Pergamon: Oxford, Chapter 3.8
    • (a) Lee, D. G.; Chen, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford, 1991: Vol. 7, Chapter 3.8. p 541.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 541
    • Lee, D.G.1    Chen, T.2
  • 108
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    • note
    • Given the formation of cis-stilbene oxide in the reaction of 1 with cis-stilbene (entry 10, Table 1), another dihydroxylation mechanism to be considered is epoxidation followed by ring expansion. However, this mechanism is incompatible with the stereoselectivity of the cis-alkene oxidation reactions. If epoxidation followed by ring expansion is involved, trans-dihydroxylation products should be formed predominantly. For example, treatment of cis-β-methylstyrene oxide with 3 under comparable conditions afforded trans-dihydroxylation product in 99% yield with 85% conversion.
  • 109
    • 26844582812 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis. Therefore, the observed stereoselectivity of the cis-alkene oxidation by 1 is unlikely to arise from a sufficiently more rapid reaction of the trans-dihydroxylation product than the cis-counterpart.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.