Concentration-Dependent Reactions of Deoxofluor with Arylglyoxal Hydrates:  A New Route to Polyfluoro Ethers

Concentration-Dependent Reactions of Deoxofluor with Arylglyoxal Hydrates:  A New Route to Polyfluoro Ethers

In concentrated solutions (CH2Cl2) at 25 °C, arylglyoxal hydrates, ArCOCHO·H2O (Ar = 4-MeO-C6H4-, 4-Me-C6H4-, 4-F-C6H4-, Ph-, (2a − f) with Deoxofluor gave fluorinated ethers, ArCF2CHFOCHFCF2Ar, (3a − f) in >90% yields as meso/racemic mixtures (∼1:1). Under very dilute conditions, mixtures of ArC...

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Veröffentlicht in:Organic letters 2001-08, Vol.3 (17), p.2713-2715
Hauptverfasser: Singh, Rajendra P, Shreeve, Jean'ne M
Format: Artikel
Sprache:eng
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Zusammenfassung:In concentrated solutions (CH2Cl2) at 25 °C, arylglyoxal hydrates, ArCOCHO·H2O (Ar = 4-MeO-C6H4-, 4-Me-C6H4-, 4-F-C6H4-, Ph-, (2a − f) with Deoxofluor gave fluorinated ethers, ArCF2CHFOCHFCF2Ar, (3a − f) in >90% yields as meso/racemic mixtures (∼1:1). Under very dilute conditions, mixtures of ArCF2CHO (major) (4a − f) and ArCF2CF2H (6a − f) (minor) were obtained. The structures of 3b (racemic) and 4a (meso) have been confirmed by single-crystal X-ray analysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016319l