Concentration-dependent reactions of deoxofluor with arylglyoxal hydrates: a new route to polyfluoro ethers.
[reaction: see text]. In concentrated solutions (CH2Cl2) at 25 degrees 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 (approximately 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.
Singh
R P
RP
Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343, USA.
Shreeve
J M
JM