HIGH REGIOSELECTIVITY IN THE ALTERNATIVE CLEAVAGE OF TERMINAL EPOXIDES WITH DIFFERENT SOURCES OF NUCLEOPHILIC FLUORIDE

Authors
SATTLER A HAUFE G
Citation
A. Sattler et G. Haufe, HIGH REGIOSELECTIVITY IN THE ALTERNATIVE CLEAVAGE OF TERMINAL EPOXIDES WITH DIFFERENT SOURCES OF NUCLEOPHILIC FLUORIDE, Journal of fluorine chemistry, 69(2), 1994, pp. 185-190
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of fluorine chemistry → ACNP
ISSN journal
00221139
Volume
69
Issue
2
Year of publication
1994
Pages
185 - 190
Database
ISI
SICI code
0022-1139(1994)69:2<185:HRITAC>2.0.ZU;2-B
Abstract
The ring-opening of epoxides derived from esters of 10-undecenoic acid using Olah's reagent yields predominantly the 10-fluoro-11-hydroxy de rivatives, while the other regio isomers are obtained predominantly wi th mixtures of triethylamine trishydrogen fluoride and other amines. T he best yields and best regioselectivity far the 11-fluoro-10-hydroxy compound, however, are found in conversion of the epoxide with potassi um hydrogen difluoride/18-crown-6 in DMF.