Abstract: Several fluorinated and trifluoromethylated indanone, tetralone and naphthone derivatives have been prepared via Claisen condensations and selective fluorinations in yields ranging from 22–60%. In addition, we report the synthesis of new, selectively fluorinated bindones in yields ranging from 72–92%. Of particular interest is the fluorination and trifluoroacetylation regiochemistry observed in these fluorinated products. We also note unusual transformations including a novel one pot, dual trifluoroacetylation, trifluoroacetylnaphthone synthesis via a deacetylation as well as an acetyl-trifluoroacetyl group exchange. Solid-state structural features exhibited by these compounds were investigated using crystallographic methods. Crystallographic results, supported by spectroscopic data, show that trifluoroacetylated ketones prefer a chelated cis-enol form whereas fluorinated bindone products exist primarily as the cross-conjugated triketo form.
Keywords: 2-trifluoroacetyl-1,3-Diketone; 1,3,5-triketone; tautomerism; X-ray crystallography
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Sloop, J.C.; Boyle, P.D.; Fountain, A.W.; Gomez, C.; Jackson, J.L.; Pearman, W.F.; Schmidt, R.D.; Weyand, J. Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features. Appl. Sci. 2012, 2, 61-99.
Sloop JC, Boyle PD, Fountain AW, Gomez C, Jackson JL, Pearman WF, Schmidt RD, Weyand J. Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features. Applied Sciences. 2012; 2(1):61-99.
Sloop, Joseph C.; Boyle, Paul D.; Fountain, Augustus W.; Gomez, Cristina; Jackson, James L.; Pearman, William F.; Schmidt, Robert D.; Weyand, Jonathan. 2012. "Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features." Appl. Sci. 2, no. 1: 61-99.