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Appl. Sci. 2012, 2(1), 61-99; doi:10.3390/app2010061
Article

Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features

1,* , 2
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3
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4
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5
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4
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2
 and
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1 School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA 2 Department of Chemistry, North Carolina State University, P.O. Box 8204, Raleigh, NC 27695, USA 3 Edgewood Chemical and Biological Center, 5183 Blackhawk Road, Aberdeen Proving Ground, MD 21010, USA 4 Department of Chemistry and Life Science, United States Military Academy, 646 Swift Road, West Point, NY 10996, USA 5 US Army Corps of Engineers, 101 West Oglethorpe Avenue, Savannah, GA 31401, USA
* Author to whom correspondence should be addressed.
Received: 6 December 2011 / Revised: 12 January 2012 / Accepted: 16 January 2012 / Published: 1 February 2012
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)

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 2-trifluoroacetyl-1,3-Diketone; 1,3,5-triketone; tautomerism; X-ray crystallography
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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