P-M-BRC-123 Stereoselective Dehydration of 2,5-Hexanediol in High-Temperature Liquid Water Enhanced by Carbon Dioxide

Monday, June 3, 2013
Ballroom C (Galt House Hotel)
Aritomo Yamaguchi, Norihito Hiyoshi, Naoki Mimura, Osamu Sato and Masayuki Shirai, National Institute of Advanced Industrial Science and Technology, Japan.
Intramolecular dehydration of chiral 2R,5R-hexanediol(HDO) or 2S,5S-HDO was dehydrated to cis-2,5-dimethyltetrahydrofuran(DMTHF) in water at 523 K, which could be enhanced by adding high-pressure carbon dioxide.  High selectivity of cis-2,5-DMTHF in the product of total 2,5-DMTHF indicated that the intramolecular dehydration proceeded mainly via an SN2 substitution process.

Extended Abstracts: