H. Suga, T. Hamatani, M. Schlosser
1990
Citations
0
Influential Citations
32
Citations
Journal
Tetrahedron
Abstract
Abstract When treated with potassium tert-butoxide in tetrahydrofuran, p-toluene-sulfonates derived from fluorohydrins afford fluoroolefins (e.g., Z- or E-3) with high yields. Fluorohydrins are readily and stereoselectively accessible by anti-periplanar addition of hydrogen fluoride to oxiranes. Terminal epoxides give preferentially 2-fluoro-1-alcanols (e.g., 4) if an hydrogen fluoride/pyridine mixture is used in toluene medium while mainly 1-fluoro-2-alkanols (e.g., 5) result from the reaction with “Hunig's hydrofluoride” (i.e., the adduct of hydrogen fluoride an N-ethyldiisopropyl- amine). With 2-hydroxymethyl substituted oxiranes, predominantly if not exclusively, 3-fluoro-1,2-alkanediols (e.g 11) are obtained.