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Volumn 48, Issue 16, 2007, Pages 2885-2888

Mesityltriphenylbismuthonium tetrafluoroborate as an efficient bismuth(V) oxidant: remarkable steric effects on reaction rates and chemoselectivities in alcohol oxidation

Author keywords

Alcohol; Bismuthonium salts; Carbonyl compounds; Chemoselectivity; Oxidation

Indexed keywords

1,3,5 TRIMETHYLBENZENE; ALCOHOL; ALDEHYDE; BISMUTH; HYDROGEN; KETONE; MESITYLTRIPHENYLBISMUTHONIUM TETRAFLUOROBORATE; N,N,N',N' TETRAMETHYLGUANIDINE; UNCLASSIFIED DRUG;

EID: 33947196275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.085     Document Type: Article
Times cited : (16)

References (34)
  • 4
    • 33947241133 scopus 로고    scopus 로고
    • Suzuki H., and Matano Y. (Eds), Elsevier, New York Chapter 5, pp 371-440
    • Komatsu N. In: Suzuki H., and Matano Y. (Eds). Organobismuth Chemistry (2001), Elsevier, New York Chapter 5, pp 371-440
    • (2001) Organobismuth Chemistry
    • Komatsu, N.1
  • 18
    • 37049089545 scopus 로고
    • In the presence of N-butyl-N′,N′,N″,N″-tetramethylguanidine, these alcohols were oxidized to the corresponding carbonyl compounds in 78-92% yields after 7.5-12 h
    • Barton D.H.R., Finet J.-P., Motherwell W.B., and Pichon C. J. Chem. Soc., Perkin Trans. 1 (1987) 251 In the presence of N-butyl-N′,N′,N″,N″-tetramethylguanidine, these alcohols were oxidized to the corresponding carbonyl compounds in 78-92% yields after 7.5-12 h
    • (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 251
    • Barton, D.H.R.1    Finet, J.-P.2    Motherwell, W.B.3    Pichon, C.4
  • 21
    • 33947259901 scopus 로고    scopus 로고
    • note
    • w = 0.0526, R = 0.0254 (I > 2.00σ(I)), GOF = 1.029. Crystallographic data for the structure of 1a have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication No. CCDC 635005. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 22
    • 33947239579 scopus 로고    scopus 로고
    • note
    • 3), triphenylbismuthane and benzene were formed. See Ref. 4.
  • 23
    • 33947240109 scopus 로고    scopus 로고
    • note
    • 1H NMR and GC.
  • 24
    • 33947203545 scopus 로고    scopus 로고
    • note
    • 2). The carbonyl compounds were easily separated from triphenylbismuthane and could be isolated in a pure form.
  • 25
    • 33947229201 scopus 로고    scopus 로고
    • note
    • At present, we assume that the ground state of 1a/TMG/alcohol is destabilized compared to the alkoxybismuth(V) intermediate in a nonpolar solvent such as toluene. The solvent effect will be investigated systematically in the future work.
  • 26
    • 33947241642 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the reaction mixture. This byproduct was presumably formed by C-arylation of the initial product, dodecanal, with 1a/TMG.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.