- Preparations of SF5- and CF3-substituted arenes utilizing the 7-oxabicyclo[2.2.1]hept-2-ene synthones
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The synthesis of SF5- and CF3-substituted benzenes and naphthalenes from various 7-oxanorbornene derivatives utilizing SF 5Cl and CF3I radical addition reactions, followed by dehydrohalogenation and aromatizatio
- Ponomarenko, Maxim V.,Lummer, Katrin,Fokin, Andrey A.,Serguchev, Yurii A.,Bassil, Bassem S.,Roeschenthaler, Gerd-Volker
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p. 8103 - 8112
(2013/12/04)
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- 1-Ethoxy-3-trifluoromethyl-1,3-butadiene and congeners as Diels-Alder components opening an entry to functionalized (trifluoromethyl)benzenes and -pyridines
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1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo-and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifluoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with dimethyl acetylenedicarboxylate and methyl propiolate to provide trifluoromethyl-substituted phthalates (2, 6 and 10) or benzoates (3, 7, 8 and 11). Satisfactory yields [of 4-(trifluoromethyl)pyridinecarboxylic acids 4 and 12] can even be achieved with methyl cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Volle, Jean-Noel,Schlosser, Manfred
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p. 1490 - 1492
(2007/10/03)
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- The Diels-Alder Route to Trifluoromethyl-Substituted Carbo- and Heterocycles
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Starting with 1,1,1-trifluoroacetone, 3-(trifluoromethyl)-1-(trimethylsilyloxy)-1,3-butadiene (2) has been prepared as a mixture of (Z) and (E) isomers.The diene undergoes cycloaddition reactions with a variety of dienophiles affording trifluoromethyl-substituted carbocyclic and heterocyclic compounds 7-11 in yields ranging from moderate to good. - Keywords: Trifluoromethyl substituents / Carbocycles / Heterocycles / Diels-Alder reactions / Electron-rich/electron-poor diene
- Schlosser, Manfred,Keller, Holger
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p. 1587 - 1590
(2007/10/02)
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