Reaction of diethylaminosulfur trifluoride with diols
Diethylaminosulfur trifluoride (DAST) reacts with dialcohols to give difluorides, sulfite esters or cyclic ethers depending on the number of carbons separating the two alcohol groups.Vicinal and 1,3-diols give large amounts of sulfite ester products while butane-1,4-diol gives almost exclusively the cyclic ether tetrahydrofuran.Terminal dialcohols longer than four carbons give primarily difluoride products.Semiempirical calculations indicate a preference for cyclic intermediates when four or less carbons separate the two alcohol moieties.These cyclic intermediates lead directly to the cyclic ethers and sulfite ester products.
Shellhamer, Dale F.,Anstine, D. Timothy,Gallego, Kelly M.,Ganesh, Brian R.,Hanson, Aaron A.,et al.
p. 861 - 866
(2007/10/02)
Oxidative fluorination in amine-HF mixtures
The selective electrochemical fluorination of alkenes, phenanthroline, naphthalene and chlorobenzene in neat amine-HF mixtures is described, together with the chemistry of 4,4-difluorocyclohexadienone.
Meurs,Eilenberg
p. 705 - 714
(2007/10/02)
Fluorination of 1,3-Dienes with Xenon Difluoride and (Difluoroiodo)Benzene
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Shellhamer, Dale F.,Conner, R. Jeffrey,Richardson, Ruthann E.,Heasley, Victor L.