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Collect. Czech. Chem. Commun. 1977, 42, 2530-2536
https://doi.org/10.1135/cccc19772530

Photochemical addition of secondary alcohols to methyl trifluoroacrylate

V. P. Šendrik, O. Paleta and V. Dědek

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  • Hajduch Jan, Duda Zdeněk, Beran Jiří, Kvíčala Jaroslav, Paleta Oldřich: Synthesis of 5-alkyl-3,4-difluorofuran-2(5H)-ones by lactonisation. Effects of substituents on cyclisation ability of fluorinated 4-hydroxyalkanoates. DFT calculations of the cyclisation energies. Journal of Fluorine Chemistry 2014, 162, 45. <https://doi.org/10.1016/j.jfluchem.2014.03.009>
  • Hajduch Jan, Paleta Oldřich: Unusual β,β′-coupling and β-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates. Journal of Fluorine Chemistry 2011, 132, 143. <https://doi.org/10.1016/j.jfluchem.2010.12.003>
  • Paleta Oldřich, Hajduch Jan, Bőhm Stanislav: Novel rearrangement of secondary alkoxyalkyl radicals during addition to a double bond. Steric shielding in the formation of tertiary alkoxyethyl radicals. Tetrahedron Letters 2002, 43, 481. <https://doi.org/10.1016/S0040-4039(01)02150-5>
  • Paleta Oldřich, Duda Zdeněk, Holý Antonín: New fluorinated nucleoside analogues with 2-butenolide rings prepared by nucleophilic vinylic fluorine displacement in 4,4-dialkyl-2,3-difluorobut-2-en-4-olides. Mendeleev Communications 2001, 11, 17. <https://doi.org/10.1070/MC2001v011n01ABEH001377>
  • Shellhamer Dale F, Allen Jeannette L, Allen Rachel D, Bostic Melissa J, Miller Elizabeth A, O’Neill Colleen M, Powers Benjamin J, Price Eric A, Probst John W, Heasley Victor L: Electrophilic versus free radical reactions of halogens and halogen systems with perfluoroalkenes and a perfluoroalkylethylene. Journal of Fluorine Chemistry 2000, 106, 103. <https://doi.org/10.1016/S0022-1139(00)00319-5>
  • Cı́rkva Vladimı́r, Böhm Stanislav, Paleta Oldřich: Radical addition reactions of fluorinated species. Part 8. Regioselectivity of radical additions to perfluoroalkylethylenes and quantum chemical calculations. Highly selective two-step synthesis of 4-(perfluoroalkyl)butane-1,2-diols. Journal of Fluorine Chemistry 2000, 102, 159. <https://doi.org/10.1016/S0022-1139(99)00237-7>
  • Paleta Oldřich, Pelter Andrew, Kebrle Josef, Duda Zdeněk, Hajduch Jan: Fluorine-Containing Butanolides and Butenolides. Vinylic Fluorine Displacement in 4,4-Dialkyl-2,3-difluoro-2-buten-4-olides and a Novel Rearrangement Induced by Organolithium Addition to a Carbonyl Group. Tetrahedron 2000, 56, 3197. <https://doi.org/10.1016/S0040-4020(00)00167-8>
  • Cı́rkva Vladimı́r, Paleta Oldrich: Radical addition reactions of fluorinated species. Part 7. Highly selective two-step synthesis of 1-(polyfluoroalkyl)ethane-1,2-diols; regioselectivity of the additions of methylated 1,3-dioxolanes to perfluoroolefins. Journal of Fluorine Chemistry 1999, 94, 141. <https://doi.org/10.1016/S0022-1139(98)00356-X>
  • Paleta Oldřich, Církva Vladimír, Budková Zuzana, Böhm Stanislav: Radical addition reactions of fluorinated species Part 6. Regioselectivity of the addition of nucleophilic radicals to halogenopropenes and evidence for a steric effect of the chlorine substituent. Journal of Fluorine Chemistry 1997, 86, 155. <https://doi.org/10.1016/S0022-1139(97)00083-3>
  • Paleta Oldřich, Církva Vladimír, Kvicala Jaroslav: Radical additions to fluoro-olefins. photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane. Journal of Fluorine Chemistry 1996, 80, 125. <https://doi.org/10.1016/S0022-1139(96)03511-7>
  • Sato Masayuki, Taniguchi Tomoko, Hirokawa Taiko, Kaneko Chikara: A facile synthesis of α,β-difluoro-α,β-unsaturated carbonyl compounds by use of molecular fluorine addition. Tetrahedron Letters 1995, 36, 6705. <https://doi.org/10.1016/00404-0399(50)1357-N>
  • Paleta Oldřich, Budková Zuzana, Kvičala Jaroslav, Timpe Hans-Joachim: Experimental evidence for a free-radical chain mechanism in the photo-initiated addition of alcohols. Tetrahedron Letters 1991, 32, 251. <https://doi.org/10.1016/0040-4039(91)80868-7>
  • Ikan Raphael, Weinstein Vera, Ravid Uzi: SYNTHESIS OF SATURATED γ-LACTONES. A REVIEW. Organic Preparations and Procedures International 1981, 13, 59. <https://doi.org/10.1080/00304948109356502>
  • SENDRIK V. P., PALETA O., DEDEK V.: ChemInform Abstract: HALOACRYLIC ACIDS. X. PHOTOCHEMICAL ADDITION OF SECONDARY ALCOHOLS TO METHYL TRIFLUOROACRYLATE. Chemischer Informationsdienst 1977, 8. <https://doi.org/10.1002/chin.197748083>