170654-32-7Relevant academic research and scientific papers
Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions
Furuta,Kuroboshi,Hiyama
, p. 2687 - 2694 (2007/10/03)
Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.
Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination
Furuta, Satoru,Kuroboshi, Manabu,Hiyama, Tamejiro
, p. 1939 - 1951 (2007/10/03)
The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.
Oxidative Desulfurization-Fluorination of 1-Substituted 2,2,2-Tris(methylthio)ethanol Induces Difluorination under Oxidation or Rearrangement
Kuroboshi, Manabu,Furuta, Satoru,Hiyama, Tamejiro
, p. 6121 - 6122 (2007/10/02)
Oxidative desulfurization-fluorination of RCH(OH)C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave RC(O)CF2SMe, whereas treatment of the same substrates with Et2NSF3 afforded RCH(SMe)CF2SMe.
