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

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

Received: 6 December 2011; in revised form: 12 January 2012 / Accepted: 16 January 2012 / Published: 1 February 2012
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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