Ring constructions by the use of fluorine substituent as activator and controller

Authors
Citation
J. Ichikawa, Ring constructions by the use of fluorine substituent as activator and controller, PUR A CHEM, 72(9), 2000, pp. 1685-1689
Citations number
14
Categorie Soggetti
Chemistry
Journal title
PURE AND APPLIED CHEMISTRY
ISSN journal
00334545 → ACNP
Volume
72
Issue
9
Year of publication
2000
Pages
1685 - 1689
Database
ISI
SICI code
0033-4545(200009)72:9<1685:RCBTUO>2.0.ZU;2-R
Abstract
By using the properties of fluorine such as electronic effects: and leaving -group ability, two types of ring-forming reactions have been achieved star ting from fluoroolefins: (i) fluorinated vinyl ketones with a vinyl and/or an aryl group, which undergo fluorine-directed and/or -activated Nazarov, F riedel-Crafts, and tandem cyclizations in their combination to construct hi ghly functionalized and fused ring systems and (ii) gem-difluoroolefins bea ring a nucleophilic center on the carbon delta to the flourines undergo int ramolecular substitution for the fluorine via "anti-Baldwin" 5-endo-trig cl osures leading to ring-fluorinated heterocycles. Throughout these reactions , fluorines function as an activator of the substrates and a controller ove r the reaction pathways.