121410-95-5Relevant articles and documents
Evaluation of cyclopentyl methyl ether (CPME) as a solvent for radical reactions
Kobayashi, Shoji,Kuroda, Hiroyuki,Ohtsuka, Yuta,Kashihara, Takashi,Masuyama, Araki,Watanabe, Kiyoshi
, p. 2251 - 2259 (2013/03/29)
We have explored the potential of cyclopentyl methyl ether (CPME) as a solvent for radical reactions. Hydrostannation, hydrosilylation, hydrothiolation, and tributyltin hydride mediated reductions were successfully carried out in CPME. GC-MS analysis indicated that CPME degraded into methyl pentanoate, cyclopentanone, 2-cyclopenten-1-ol, and cyclopentanol under thermal radical conditions, albeit only slightly. We also achieved radical-containing one-pot reactions in CPME as a demonstration of its applicability to multi-step reactions.
The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry
Barton, Derek H. R.,Jang, Doo Ok,Jaszberenyi, Joseph Cs.
, p. 7193 - 7214 (2007/10/02)
Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.
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.