28981-21-7Relevant academic research and scientific papers
Facile Barton-McCombie deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate ion
Hee, Sock Park,Hee, Yoon Lee,Yong, Hae Kim
, p. 3187 - 3190 (2005)
(Chemical Equation Presented) A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu 4N)2S2O8 and HCO2Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl derivatives from CO2?- rather than from SO4?-.
Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with n-Bu3SnH-Et3B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages
Nozaki, Kyoko,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2578 - 2583 (2007/10/02)
The reduction of dithiocarbonates or thiocarbonates by n-Bu3SnH-Et3B easily gives the corresponding hydrocarbons.The intermediate alkoxythiocarbonyl radical equivalents are trapped by properly located carbon-carbon multiple bonds.The dithiocarbonates derived from either homopropargylic or homoallylic alcohols produce tetrahydrofuranones upon treatment with n-Bu3SnH-Et3B.Application of this new method to the conversion of carbonyl compounds into olefins is also described.
New Procedure for the Transformation of Alcohols to Alkyl Halides via Xanthate Esters and Free-Radical Intermediates
Cristol, Stanley J.,Seapy, Dave G.
, p. 132 - 136 (2007/10/02)
O-Alkyl-S-methyl xanthates have been used to convert alcohols to alkyl halides via free-radical pathways.The xanthate esters were readily prepared in high yields and were converted in 8-80percent yields to the corresponding alkyl halides by (a) photolysis with 254-nm light in carbon tetrachloride or bromotrichloromethane and (b) by treatment with Cu(I)-Cu(II) halide in acetonitrile.The photochemical transformation gave low yields with highly aliphathic compounds due to carbon tetrachloride-mediated free-radical halogenation reactions.The transformation promoted by Cu(I)-Cu(II) halide competed with an electron-transfer oxidation process.The reaction could not be induced with AIBN or benzoyl peroxide or by treatment with molybdenum pentachloride.Mechanistic implications are discussed.
