373-29-5Relevant articles and documents
A useful conversion of alcohols to alkyl fluorides
Flosser, David A,Olofson, Roy A
, p. 4275 - 4279 (2007/10/03)
A useful conversion of alcohols to alkyl fluorides via their fluoroformates is introduced. The fluoroformates are obtained in nearly quantitative yield from the alcohols by treatment with COF2 (generated in situ from bis(trichloromethyl) carbonate) in ether with KF as an added acid scavenger. The neat fluoroformates are cleaved to the fluorides by heating at 120-125°C using hexabutylguanidinium fluoride (HBGF) as the catalyst.
Reaction of diethylaminosulfur trifluoride with diols
Shellhamer, Dale F.,Anstine, D. Timothy,Gallego, Kelly M.,Ganesh, Brian R.,Hanson, Aaron A.,et al.
, p. 861 - 866 (2007/10/02)
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.