Synthesis and Structure of Novel 1-Aryl-4,4,4-trichloro-1,3-butanediones |
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Authors: | Alex F. C. Flores Mauro J. Martins Leandro M. Frigo Pablo Machado Patrick T. Campos Juliana L. Malavolta |
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Affiliation: | 1. NUQUIMHE, Departamento de Química , Universidade Federal de Santa Maria , Santa Maria , Brazil alexflores@smail.ufsm.br;3. NUQUIMHE, Departamento de Química , Universidade Federal de Santa Maria , Santa Maria , Brazil |
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Abstract: | Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80–97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and 1H/13C nuclear magnetic resonance (NMR) measurements. The 1H/13C NMR data showed that trichloromethyl-β-diketones 2a–k in solution are predominantly ketoenol. However, the spectroscopic data from 4,4,4-trichloro-2-methyl-1-phenyl-1,3-butabedione (2l) with methyl substituent between carbonyls showed a bias toward the diketo form in solution. X-ray diffraction of monocrystals from 2g and 2i showed that these compounds are cis-ketoenol tautomers. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communcations® to view the free supplemental file. |
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Keywords: | Acetal acylation roman" >β-diketones keto–enol equilibrium trichloromethyl- roman" >β-diketones |
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