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Keywords = 2-trifluoroacetyl-1,3-Diketone

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39 pages, 645 KiB  
Article
Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features
by Joseph C. Sloop, Paul D. Boyle, Augustus W. Fountain, Cristina Gomez, James L. Jackson, William F. Pearman, Robert D. Schmidt and Jonathan Weyand
Appl. Sci. 2012, 2(1), 61-99; https://doi.org/10.3390/app2010061 - 1 Feb 2012
Cited by 7 | Viewed by 9707
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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