Synthesis of new trifluoromethyl containing dialkyl …新型三氟甲基二烷基合成.pdfVIP

J. Serb. Chem. Soc. 71 (4) 323 – 330 (2006) UDC 547.412.122+542.913:547.77 JSCS – 3428 Original scientific paper Synthesis of new trifluoromethyl-containing 1-(3,5-dialkyl-4-hydroxybenzyl)-pyrazole and -pyrazol-5-one deriatives and their corresponding aroxyls VASILE DINOIU 1* and JIAN-MING LÜ2 1Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan and 2Department of Chemistry, University of Houston, Houston, TX 77 204, USA (e-mail: vdinoiu@) (Received 22 February, revised 31 August 2005) Abstract : 3,5-Dialkyl-4-hydroxybenzylhydrazine 1 reacted with hexafluoroacetyla- cetone, and trifluoroacetylacetone yielding the pyrazoles 2 bearing trifluoromethyl and/or methyl substituents in positions 3 and 5. The same hydrazine derivatives 1 af- forded the pyrazol-5-ones 3 with trifluoroacetoacetic acid ethyl ester. On oxidation with lead tetraacetate in CH Cl , some stable aroxyls were obtained and their ESR 2 2 spectra are described. Keywords : fluorination, pyrazole, pyrazolone, trifluoromethyl-1,3-diketones. INTRODUCTION Fluorine is the most electronegative element and the van der Waals radius of fluorine is close to that of hydrogen, hence the introduction of a fluorine-contain- ing group into an organic molecule brings about some remarkable changes in its 1 physical and chemical properties. Many new fluorinated materials which take ad- vantage of these useful changes, e.g., drugs and agrochemicals, have been de- signed2 and synthesized.3 Continuing our studies directed to