A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithio carbonates

Citation
K. Kanie et al., A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithio carbonates, B CHEM S J, 73(2), 2000, pp. 471-484
Citations number
55
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
0009-2673 → ACNP
Volume
73
Issue
2
Year of publication
2000
Pages
471 - 484
Database
ISI
SICI code
0009-2673(200002)73:2<471:ACSOTE>2.0.ZU;2-L
Abstract
Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is app lied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic g roup, fluorination leading to the corresponding alkyl fluorides R-F is achi eved, whereas a combination of 50% HF/pyridine and N-bromosuccinimide affor ds the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).