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Volumn 50, Issue 26, 2009, Pages 3665-3668

Microwave-assisted aliphatic fluorine-chlorine exchange using triethylamine trihydrofluoride (TREAT-HF)

Author keywords

Fluorination; gem Difluoride; Microwave irradiation; Pyrazole; Silicon carbide

Indexed keywords

CHLORINE; FLUORIDE; FLUORINE; SILICON CARBIDE; TRIETHYLAMINE;

EID: 65649094517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.103     Document Type: Article
Times cited : (66)

References (42)
  • 17
    • 65649139860 scopus 로고    scopus 로고
    • PCT Int. Appl. 2004, WO 2004/035589 (Syngenta Participations AG);
    • Ehrenfreund, J.; Tobler, H.; Walter, H. PCT Int. Appl. 2004, WO 2004/035589 (Syngenta Participations AG); Chem. Abstr. 2004, 140, 375164.
    • (2004) Chem. Abstr , vol.140 , pp. 375164
    • Ehrenfreund, J.1    Tobler, H.2    Walter, H.3
  • 25
    • 65649136419 scopus 로고    scopus 로고
    • PCT Int. Appl, WO 9743231 Rhone-Poulenc Chimie SA, Fr, Chem. Abstr. 1997, 128, 34573
    • Saint Jalmes, L. PCT Int. Appl. 1997, WO 9743231 (Rhone-Poulenc Chimie SA, Fr.) (Chem. Abstr. 1997, 128, 34573).
    • (1997)
    • Saint Jalmes, L.1
  • 26
    • 67349161331 scopus 로고    scopus 로고
    • For a recent review with 930 references and a tabular survey of ca. 200 microwave chemistry review articles, books and book chapters, see: 10.1007/s11030-009-9138-8
    • For a recent review with 930 references and a tabular survey of ca. 200 microwave chemistry review articles, books and book chapters, see:. Kappe C.O., and Dallinger D. Mol. Diversity 13 (2009) 10.1007/s11030-009-9138-8
    • (2009) Mol. Diversity , Issue.13
    • Kappe, C.O.1    Dallinger, D.2
  • 29
    • 65649124423 scopus 로고    scopus 로고
    • It should be noted, however, that extremely rapid fluorinations with similar high selectivities can be achieved by irradiating the reaction mixture with constant 300 W of microwave power for 30 s. This leads to a maximum monitored reaction temperature of 250 °C as a result of the high microwave absorptivity of the polar TREAT-HF reagent/solvent Refs. 8,9
    • It should be noted, however, that extremely rapid fluorinations with similar high selectivities can be achieved by irradiating the reaction mixture with constant 300 W of microwave power for 30 s. This leads to a maximum monitored reaction temperature of 250 °C as a result of the high microwave absorptivity of the polar TREAT-HF reagent/solvent (Refs. 8,9).
  • 30
    • 4644338541 scopus 로고    scopus 로고
    • Isolated yields on experiments carried out on a comparatively small scale were only moderate (50-60%) as a consequence of the high volatility of the fluorinated product. See also: (compound 2)
    • Isolated yields on experiments carried out on a comparatively small scale were only moderate (50-60%) as a consequence of the high volatility of the fluorinated product. See also:. Kitazume T., and Ebata T. J. Fluorine Chem. 125 (2004) 1509-1511 (compound 2)
    • (2004) J. Fluorine Chem. , vol.125 , pp. 1509-1511
    • Kitazume, T.1    Ebata, T.2
  • 34
    • 65649087748 scopus 로고    scopus 로고
    • note
    • CAUTION! Corrosion of microwave vials during usage represents a serious safety risk as the pressure rating of the heavy-walled vials (20 bar) will not be maintained. Prolonged exposure of TREAT-HF at high temperatures and pressures (e.g., ca. 10 bar at 250 °C) or repeated vial usage must therefore be strictly avoided.
  • 37
    • 65649101754 scopus 로고    scopus 로고
    • note
    • Microwave experiments in SiC vessels closely simulate oil bath experiments since the penetration of the electromagnetic field into the inner part of the vial is small. Due to the high thermal conductivity of SiC, rapid heating of the reaction mixture can nevertheless be obtained, similar to a standard microwave chemistry experiment. Further details on SiC reaction vessels for use in single-mode microwave reactors will be reported in subsequent publications.
  • 38
    • 65649150245 scopus 로고    scopus 로고
    • PCT Int. Appl. 2005, WO 2005/042468 (Bayer Cropscience AG);
    • Lantzsch, R.; Jörges, W.; Pazenok, S. PCT Int. Appl. 2005, WO 2005/042468 (Bayer Cropscience AG); Chem. Abstr. 2005, 142, 409463.
    • (2005) Chem. Abstr , vol.142 , pp. 409463
    • Lantzsch, R.1    Jörges, W.2    Pazenok, S.3
  • 39
    • 65649094315 scopus 로고    scopus 로고
    • PCT Int. Appl. 2005, WO 2005/044804 (Bayer Cropscience AG);
    • Lantzsch, R.; Pazenok, S.; Memmel, F. PCT Int. Appl. 2005, WO 2005/044804 (Bayer Cropscience AG); Chem. Abstr. 2005, 142, 482038.
    • (2005) Chem. Abstr , vol.142 , pp. 482038
    • Lantzsch, R.1    Pazenok, S.2    Memmel, F.3
  • 40
    • 65649136080 scopus 로고    scopus 로고
    • note
    • 3, 360 MHz): δ 1.37 (t, J = 7.1 Hz, 3H), 3.98 (s, 3H), 4.33 (q, J = 7.1 Hz, 2H), 7.12 (t, J = 54.0 Hz, 1H), 7.91 (s, 1H), MS (EI, 70 eV): m/z = 204, mp = 58-59 °C.
  • 42
    • 65649142076 scopus 로고    scopus 로고
    • note
    • The fluorination was performed on an unseparable mixture of the 3-dichloromethyl pyrazole 14 and its 5-dichloromethyl isomer. See Supplementary data for more details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.