ISSN:
0947-3440
Keywords:
Organofluorine compounds
;
1-Fluoroalkyl esters
;
2-Fluoroalkyl esters
;
Ene esters
;
Diene esters
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 2-fluoroalkyl esters (1-4) of carboxylic acids are readily accessible by the base-catalyzed acylation of fluorohydrines. A two-step procedure is required to prepare the 1-fluoroalkyl esters (10-14, 16): conversion of alk-1-enyl carboxylates („ene esters“) into the 2-bromo-1-fluoroalkyl esters 5-9, 15, 17-19 by simultaneous treatment with N-bromosuccinimide and hydrogen fluoride followed by the reductive replacement of bromine by tributyltin hydride. Alka-1,3-dienyl carboxylates („diene esters“) undergo 1,4-addition of bromine and fluorine. The resulting 4-bromo-1-fluoroalk-2-enyl carboxylates 20-25 undergo a substitution reaction with sodium benzenesulfinate to afford the sulfones 26-28 or oxidation with dimethyl sulfoxide to yield the 4-oxo derivatives 29-30.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199505123
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