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Volumn 56, Issue 2, 2000, Pages 275-283

Fluoroform: An efficient precursor for the trifluoromethylation of aldehydes

Author keywords

Fluoroform; Trifluoromethylation

Indexed keywords

ALDEHYDE DERIVATIVE; FLUOROFORM;

EID: 0343048990     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00951-5     Document Type: Article
Times cited : (122)

References (72)
  • 29
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    • Generously provided by Rhone-Poulenc. This gas has a low boiling point (-82°C) but is very soluble in polar solvents as DMF.
    • Generously provided by Rhone-Poulenc. This gas has a low boiling point (-82°C) but is very soluble in polar solvents as DMF.
  • 39
    • 85038055108 scopus 로고    scopus 로고
    • Although we have no evidence of the formation of these species, this formulae represents the relative stoichiometry of the reactants.
    • Although we have no evidence of the formation of these species, this formulae represents the relative stoichiometry of the reactants.
  • 42
    • 0032492981 scopus 로고    scopus 로고
    • Preliminary results of this work have already been published:
    • Preliminary results of this work have already been published: Folléas, B.; Marek, I.; Normant, J. F.; Saint-Jalmes, L. Tetrahedron Lett. 1998, 39, 2973, and more recently, a parallel study from Rhône-Poulenc Company has been disclosed concerning the potassium trifluoromethylide: Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2973
    • Folléas, B.1    Marek, I.2    Normant, J.F.3    Saint-Jalmes, L.4
  • 43
    • 0032487852 scopus 로고    scopus 로고
    • and more recently, a parallel study from Rhône-Poulenc Company has been disclosed concerning the potassium trifluoromethylide
    • Preliminary results of this work have already been published: Folléas, B.; Marek, I.; Normant, J. F.; Saint-Jalmes, L. Tetrahedron Lett. 1998, 39, 2973, and more recently, a parallel study from Rhône-Poulenc Company has been disclosed concerning the potassium trifluoromethylide: Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771.
    • (1998) Tetrahedron , vol.54 , pp. 13771
    • Russell, J.1    Roques, N.2
  • 44
    • 0038798069 scopus 로고
    • Formed probably by the Tishchenko reaction, followed by saponification in the work-up; see
    • Formed probably by the Tishchenko reaction, followed by saponification in the work-up; see Kamm, O.; Kamm, F. Org. Synth. 1948, 1, 104.
    • (1948) Org. Synth. , vol.1 , pp. 104
    • Kamm, O.1    Kamm, F.2
  • 46
    • 85038062159 scopus 로고    scopus 로고
    • After metallation, one equivalent of hydrogen is formed which will not react with the trifluoromethyl metal.
    • After metallation, one equivalent of hydrogen is formed which will not react with the trifluoromethyl metal.
  • 47
    • 85038070303 scopus 로고    scopus 로고
    • The reaction of several organometallics with DMF as a formylating agent is a well known reaction.
    • The reaction of several organometallics with DMF as a formylating agent is a well known reaction.
  • 52
    • 85038063187 scopus 로고    scopus 로고
    • Determined by using α,α,α-trifluorotoluene as an internal standard.
    • Determined by using α,α,α-trifluorotoluene as an internal standard.
  • 67
    • 85038067713 scopus 로고    scopus 로고
    • 19F NMR).
    • 19F NMR).
  • 68
    • 85038064952 scopus 로고    scopus 로고
    • In above studies, dimsyl-K was formed in DMSO as a solvent.
    • In above studies, dimsyl-K was formed in DMSO as a solvent.
  • 71
    • 0001783764 scopus 로고
    • This environmentally friendly urea has a polarity comparable to that of HMPT and can replace it in many cases. See
    • This environmentally friendly urea has a polarity comparable to that of HMPT and can replace it in many cases. See: Sakurai, H.; Kondo, F. J. Organomet. Chem. 1975, 92, C46.
    • (1975) J. Organomet. Chem. , vol.92
    • Sakurai, H.1    Kondo, F.2
  • 72
    • 0033609938 scopus 로고    scopus 로고
    • Note added in proof: During our corrections, a recent publication showed that our postulated mechanism involving 14 as the trifluoromethylating intermediate is indeed viable.
    • Note added in proof: During our corrections, a recent publication (Mispelaere, C.; Roques, N. Tetrahedron Letters 1999, 40, 6411) showed that our postulated mechanism involving 14 as the trifluoromethylating intermediate is indeed viable.
    • (1999) Tetrahedron Letters , vol.40 , pp. 6411
    • Mispelaere, C.1    Roques, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.