Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features
| Autor: | James L. Jackson, William F. Pearman, Cristina Gomez, Joseph C. Sloop, Jonathan Weyand, Augustus W. Fountain, Robert D. Schmidt, Paul D. Boyle |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
2-trifluoroacetyl-1
3-Diketone 1 3 5-triketone lcsh:Technology lcsh:Chemistry chemistry.chemical_compound Tetralone Organic chemistry General Materials Science Chelation Instrumentation lcsh:QH301-705.5 X-ray crystallography Fluid Flow and Transfer Processes lcsh:T Process Chemistry and Technology General Engineering Regioselectivity Tautomer lcsh:QC1-999 Computer Science Applications tautomerism chemistry lcsh:Biology (General) lcsh:QD1-999 lcsh:TA1-2040 lcsh:Engineering (General). Civil engineering (General) lcsh:Physics |
| Zdroj: | Applied Sciences; Volume 2; Issue 1; Pages: 61-99 Applied Sciences, Vol 2, Iss 1, Pp 61-99 (2012) |
| ISSN: | 2076-3417 |
| DOI: | 10.3390/app2010061 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|