When treated with KOCMe3 in THF, fluorohydrin p-tosylates afford fluoro olefins, e.g., Z- or E-Me(CH2)4CF:CH(CH2)4Me, in high yields. Fluorohydrins are readily and stereoselectively accessible by antiperiplanar addn. of HF to oxiranes. Terminal epoxides give preferentially 2-fluoro-1-alkanols with HF-pyridine mixt. in PhMe, while mainly 1-fluoro-2-alkanols result from reaction with Huenig's hydrofluoride (i.e., the adduct of HF and (Me2CH)2NEt. With 2-hydroxymethyl-substituted oxiranes, 3-fluoro-1,2-alkanediols are obtained predominantly if not exclusively. [on SciFinder (R)]
Title
Regioselective formation of fluorohydrins and their stereoselective conversion to fluoroolefins
Published in
Tetrahedron
Volume
46
Issue
12
Pages
4247-4254
Date
1990
ISSN
0040-4020
Note
CAN 114:61493
23-3
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
131600-43-6 Role: CAT (Catalyst use), USES (Uses) (catalyst, for conversion of epoxides to fluorohydrins, regiochem. with); 114069-06-6P; 130876-19-6P; 130876-20-9P; 130876-23-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and elimination reaction of, with potassium tert-butoxide); 130876-18-5P; 130888-52-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and stereoselective tosylation of); 110500-35-1P; 130876-22-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and tosylation of); 66291-49-4P; 66291-50-7P; 112482-36-7P; 112482-37-8P; 119105-47-4P; 130876-17-4P; 130876-21-0P; 130876-24-3P; 130876-25-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 2404-44-6; 2930-05-4; 90528-62-4 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective ring cleavage of); 92943-15-2; 92943-16-3 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective ring cleavage of, with triethylamine tris(hydrofluoride)
Record creation date
2006-03-03
