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...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2012-02-01
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| Series: | Applied Sciences |
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| Online Access: | http://www.mdpi.com/2076-3417/2/1/61 |
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| author | Joseph C. Sloop Paul D. Boyle Augustus W. Fountain Cristina Gomez James L. Jackson William F. Pearman Robert D. Schmidt Jonathan Weyand |
| author_facet | Joseph C. Sloop Paul D. Boyle Augustus W. Fountain Cristina Gomez James L. Jackson William F. Pearman Robert D. Schmidt Jonathan Weyand |
| author_sort | Joseph C. Sloop |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T07:37:07Z |
| format | Article |
| id | doaj.art-8019257bb94f430c845bebd9908d0ec2 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-04-13T07:37:07Z |
| publishDate | 2012-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-8019257bb94f430c845bebd9908d0ec22022-12-22T02:56:07ZengMDPI AGApplied Sciences2076-34172012-02-0121619910.3390/app2010061Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural FeaturesJoseph C. SloopPaul D. BoyleAugustus W. FountainCristina GomezJames L. JacksonWilliam F. PearmanRobert D. SchmidtJonathan WeyandSeveral 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.http://www.mdpi.com/2076-3417/2/1/612-trifluoroacetyl-1,3-Diketone1,3,5-triketonetautomerismX-ray crystallography |
| spellingShingle | Joseph C. Sloop Paul D. Boyle Augustus W. Fountain Cristina Gomez James L. Jackson William F. Pearman Robert D. Schmidt Jonathan Weyand Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features Applied Sciences 2-trifluoroacetyl-1,3-Diketone 1,3,5-triketone tautomerism X-ray crystallography |
| title | Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features |
| title_full | Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features |
| title_fullStr | Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features |
| title_full_unstemmed | Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features |
| title_short | Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features |
| title_sort | novel fluorinated indanone tetralone and naphthone derivatives synthesis and unique structural features |
| topic | 2-trifluoroacetyl-1,3-Diketone 1,3,5-triketone tautomerism X-ray crystallography |
| url | http://www.mdpi.com/2076-3417/2/1/61 |
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