55852-04-5Relevant articles and documents
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.