a-Fluoro- and a,a-difluoroalkanals by substitution of vicinal bromofluoroalkanes and subsequent Pummerer rearrangement

2-Fluoro- or 2,2-difluoro-1-bromoalkanes readily undergo nucleophilic substitution by sodium thiophenolate to give 2-fluoro- or 2,2-difluoroalkyl Ph sulfides. The latter can be oxidized to the corresponding sulfoxides. Heating with acetic anhydride produces 2-fluoro- and 2,2-difluoro-1-(phenylthio)alkyl acetates, which can then be cleaved to give 2-fluoro- and 2,2-difluoro-1-(phenylthio)-1-alkanols or the 2-fluoro- and 2,2-difluoroalkanals if not reduced to give 2-fluoro- or 2,2-difluoro-1-alkanols. [on SciFinder (R)]


Published in:
Tetrahedron, 46, 12, 4261-4
Year:
1990
Keywords:
Note:
CAN 113:171600
25-15
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4020
written in English.
129973-39-3P; 129973-40-6P; 129973-41-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Pummerer rearrangement of); 129973-48-4P; 129973-49-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and conversion to aldehyde); 100655-82-1P; 129973-37-1P; 129973-38-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of); 129973-43-9P; 129973-44-0P; 129973-45-1P; 129973-53-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 129660-35-1P; 129973-42-8P; 129973-46-2P; 129973-47-3P; 129973-50-8P; 129973-51-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 930-69-8 (Sodium thiophenoxide) Role: RCT (Reactant), RACT (Reactant or reagent) (substitution reaction of, with bromofluoroalkanes); 1786-34-1; 108661-89-8; 129973-52-0 Role: RCT (Reactant), RACT (Reactant or reagent) (substitution reaction of, with thiophenoxide)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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