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Volumn 62, Issue 46, 2006, Pages 10747-10752

'Reductive ozonolysis' via a new fragmentation of carbonyl oxides

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKANE DERIVATIVE; ALKENE; AMINE; CARBONYL DERIVATIVE; DIMETHYL SULFOXIDE; NITROGEN DERIVATIVE; OXIDE;

EID: 33749242465     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.092     Document Type: Article
Times cited : (33)

References (52)
  • 4
    • 33746884536 scopus 로고
    • For an overview of ozonide reduction, see:. Kropf H. (Ed), Georg Thieme, Stuttgart
    • For an overview of ozonide reduction, see:. Kropf H. In: Kropf H. (Ed). Houben-Weyl Methoden Der Organische Chemie Vol. E13/2 (1988), Georg Thieme, Stuttgart 1111
    • (1988) Houben-Weyl Methoden Der Organische Chemie , vol.E13-2 , pp. 1111
    • Kropf, H.1
  • 5
    • 84937549135 scopus 로고
    • Ozonolysis of electron-poor alkenes in methanolic base results in the direct formation of methyl esters:
    • Ozonolysis of electron-poor alkenes in methanolic base results in the direct formation of methyl esters:. Marshall J.A., Garofalo A.W., and Sedrani R.C. Synlett (1992) 643
    • (1992) Synlett , pp. 643
    • Marshall, J.A.1    Garofalo, A.W.2    Sedrani, R.C.3
  • 11
    • 1842739206 scopus 로고    scopus 로고
    • and Mg/MeOH or Zn/HOAc ( ) can lead to problems with separation of byproducts or functional group compatibility
    • and Mg/MeOH or Zn/HOAc (. Dai P., Dussault P.H., and Trullinger T.K. J. Org. Chem. 69 (2004) 2851 ) can lead to problems with separation of byproducts or functional group compatibility
    • (2004) J. Org. Chem. , vol.69 , pp. 2851
    • Dai, P.1    Dussault, P.H.2    Trullinger, T.K.3
  • 28
    • 33749257473 scopus 로고
    • Any work involving peroxides should follow standard precautions:, Ellis Horwood, Chichester, UK
    • Any work involving peroxides should follow standard precautions:. Medard L.A. Accidental Explosions: Types of Explosive Substances Vol. 2 (1989), Ellis Horwood, Chichester, UK
    • (1989) Accidental Explosions: Types of Explosive Substances , vol.2
    • Medard, L.A.1
  • 30
    • 0000936726 scopus 로고
    • Swern D. (Ed), Wiley-Interscience, New York, NY
    • Shanley E.S. In: Swern D. (Ed). Organic Peroxides Vol. 3 (1970), Wiley-Interscience, New York, NY 341
    • (1970) Organic Peroxides , vol.3 , pp. 341
    • Shanley, E.S.1
  • 31
    • 33749242939 scopus 로고    scopus 로고
    • note
    • 1H NMR of crude reaction mixtures.
  • 38
    • 33749235127 scopus 로고    scopus 로고
    • note
    • 2 for 2 min and warmed to room temperature. Following confirmation of the absence of ozonide (TLC), the solution was concentrated and the residue was purified by flash chromatography using 5% diethyl ether/pentane. Alternatively, the crude reaction was quenched into pH 6 phosphate buffer and extracted with ether prior to concentration and chromatography.
  • 39
    • 33749260111 scopus 로고    scopus 로고
    • note
    • Control experiments demonstrated that the hydroperoxyacetal is relatively stable to the presence of NMMO.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.