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

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...

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Bibliographic Details
Published in:Applied sciences 2012-03, Vol.2 (1), p.61-99
Main Authors: Sloop, Joseph C., Boyle, Paul D., Fountain, Augustus W., Gomez, Cristina, Jackson, James L., Pearman, William F., Schmidt, Robert D., Weyand, Jonathan
Format: Article
Language:English
Subjects:
1,3,5-triketone
2-trifluoroacetyl-1,3-Diketone
tautomerism
X-ray crystallography
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Summary: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.
ISSN:2076-3417
2076-3417
DOI:10.3390/app2010061