Facile synthesis of alpha-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

Citation
S. Furuta et al., Facile synthesis of alpha-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions, B CHEM S J, 71(11), 1998, pp. 2687-2694
Citations number
31
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
0009-2673 → ACNP
Volume
71
Issue
11
Year of publication
1998
Pages
2687 - 2694
Database
ISI
SICI code
0009-2673(199811)71:11<2687:FSOASU>2.0.ZU;2-2
Abstract
Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5, 5-dimethylhydantoin, vari ous organic sulfides underwent a Pummerer-type rearrangement, followed by f luorination, to give alpha-fluoro sulfides. The fluoro-Pummerer rearrangeme nt, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidati ve desulfurization-fluorination reaction occurred depending on the structur e of the substrates.