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Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA
Department of Chemistry, North Carolina State University, P.O. Box 8204, Raleigh, NC 27695, USA
Edgewood Chemical and Biological Center, 5183 Blackhawk Road, Aberdeen Proving Ground, MD 21010, USA
Department of Chemistry and Life Science, United States Military Academy, 646 Swift Road, West Point, NY 10996, USA
US Army Corps of Engineers, 101 West Oglethorpe Avenue, Savannah, GA 31401, USA
* Author to whom correspondence should be addressed.
Received: 6 December 2011; in revised form: 12 January 2012 / Accepted: 16 January 2012 / Published: 1 February 2012
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.