16336-50-8Relevant articles and documents
Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries
Lin, Shishi,Lies, Shane D.,Gravatt, Christopher S.,Yoon, Tehshik P.
supporting information, p. 368 - 371 (2017/04/21)
The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative “redox auxiliary” strategy that offers a practical means to circumvent a fundamental thermodynamic limitation facing photoredox reactions.
Regio- and stereospecific cleavage of stannylepoxides with lithium phenylsulfide
Cuadrado, Purificación,González-Nogal, Ana M.
, p. 8993 - 8996 (2007/10/03)
Unsubstituted and α or β C-substituted epoxystannanes react with lithium phenylsulfide to give regio- and stereodefined α-phenylthio-β-hydroxystannanes resulting from α-opening with inversion of configuration. On the other hand, α- or β-trans-silyl epoxys
First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts
Matano, Yoshihiro,Yoshimune, Masanori,Azuma, Nagao,Suzuki, Hitomi
, p. 1971 - 1977 (2007/10/03)
Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.
