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Preparation of (Z)-1-fluoro-1-alkenyl carboxylates, carbonates and carbamates through chromium mediated transformation of dibromofluoromethylcarbinyl esters and the reactivity as double acyl group donors
- Source :
- Journal of Fluorine Chemistry. 133:38-51
- Publication Year :
- 2012
- Publisher :
- Elsevier BV, 2012.
-
Abstract
- CrCl2/Mn-mediated transformation of various dibromofluoromethylcarbinyl esters including carboxylates, carbonates and carbamates provided 1-fluoro-1-alkenyl esters via [2,3]-sigmatropic rearrangement of ester group. Reaction proceeded by using CrCl2/Mn system under mild conditions (in THF at room temperature) to give 1-fluoro-1-alkenyl esters in good yield with an excellent Z selective manner. 1-Fluoro-1-alkenyl ester thus obtained acts as a double acyl donor in the reaction with necleophiles such as amine, thiol, alcohol as well as bifunctional necleophiles such as ethylene diamine derivative.
- Subjects :
- 2,3-sigmatropic rearrangement
Organic Chemistry
Nucleophilic acyl substitution
Alcohol
Biochemistry
Medicinal chemistry
Inorganic Chemistry
Acylation
chemistry.chemical_compound
chemistry
Environmental Chemistry
Organic chemistry
Amine gas treating
Reactivity (chemistry)
Physical and Theoretical Chemistry
Bifunctional
Acyl group
Subjects
Details
- ISSN :
- 00221139
- Volume :
- 133
- Database :
- OpenAIRE
- Journal :
- Journal of Fluorine Chemistry
- Accession number :
- edsair.doi...........1c0163352352c4d914376978dc1a5279