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Volumn 69, Issue 24, 2004, Pages 8467-8474

Ruthenium-catalyzed [2 + 2] cycloadditions between 7-substituted norbornadienes and alkynes: An experimental and theoretical study

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ADDITION REACTIONS; CATALYSIS; COMPUTATIONAL METHODS; POTENTIAL ENERGY; SUBSTITUTION REACTIONS;

EID: 9344258620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048590x     Document Type: Article
Times cited : (50)

References (57)
  • 2
    • 0004136903 scopus 로고
    • JAI Press Greenwich
    • (b) Advances in Cycloaddition; JAI Press: Greenwich, 1988-1999; Vols. 1-6.
    • (1988) Advances in Cycloaddition , pp. 1-6
  • 3
    • 0002110351 scopus 로고    scopus 로고
    • For reviews on transition-metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 36
    • 9344269187 scopus 로고    scopus 로고
    • note
    • Since different cycloadducts may provide different response from the detector of the GC, an equimolar amount of two different cycloadducts may not provide exactly a 1:1 ratio of peak areas on the GC integration. Thus, equimolar amount of each cycloadduct was injected into the GC and their integration areas were compared. These numbers were then used to correct for the product ratios.
  • 37
    • 9344230134 scopus 로고    scopus 로고
    • note
    • As noted by a reviewer, the observed relative rate of cycloaddition may not be purely from an electronic effect. The coordinating ability of the 7-substutuent that competes with the anti-π-bond for the metal center could also be a factor in the observed rate difference.
  • 45
    • 9344266940 scopus 로고    scopus 로고
    • note
    • For more detailed studies on the effect of the number of equivalency of the reaction partners in Ru-catalyzed [2 + 2] cycloadditions between alkenes and alkynes, see ref 12a.
  • 48
    • 9344234791 scopus 로고    scopus 로고
    • note
    • Optimized geometries for all the structures mentioned in the text are reported in the Supporting Information.
  • 49
    • 0035794891 scopus 로고    scopus 로고
    • The regiochemistry of metallacyclopentenes 15(B) and 15a,d,f is opposite that proposed by Cheng and co-workers in the nickel-catalyzed coupling and cyclization reactions between oxanorbornenes and alkyl propiolates. The difference in regiochemistry could be due to the use of different metal catalyst (nickel vs ruthenium), and the oxygen in the oxanorbornenes used in Cheng's study could coordinate to the metal but not in our case with norbornadienes. Also, there are no theoretical calculations to support the proposed mechanism/ structure by Cheng: (a) Rayabarapu, D. K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2001, 40, 1286.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1286
    • Rayabarapu, D.K.1    Cheng, C.-H.2
  • 51
    • 0035958467 scopus 로고    scopus 로고
    • General methods were as described in a previous publication: Tranmer, G. K.; Tam, W. J. Org. Chem. 2001, 66, 5113.
    • (2001) J. Org. Chem. , vol.66 , pp. 5113
    • Tranmer, G.K.1    Tam, W.2
  • 52
    • 0001599502 scopus 로고
    • 7-Substituted norbornadienes 2a-f were prepared according to literature procedures: (a) Story, P. R.; Fahrenholtz, S. R. J. Org. Chem. 1963, 28, 1716.
    • (1963) J. Org. Chem. , vol.28 , pp. 1716
    • Story, P.R.1    Fahrenholtz, S.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.