114221-61-3Relevant academic research and scientific papers
Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant
Wang, Jin,Wei, Chiyu,Li, Xuming,Zhao, Pengyi,Shan, Chuan,Wojtas, Lukasz,Chen, Hao,Shi, Xiaodong
supporting information, p. 5946 - 5950 (2020/04/23)
Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.
Formation and Electrophilic Reactions of Benzeneselenenyl p-Toluenesulfonate. Perparation and Properties of Addition Products with Acetylenes
Back, Thomas G.,Muralidharan, K. Raman
, p. 2781 - 2787 (2007/10/02)
Benzeneselenenyl p-toluenesulfonate (1) was generated in situ by the reaction of silver p-toluenesulfonate with benzeneselenenyl chloride in acetonitrile.The reagent reacted with acetylenes by electrophilic 1,2-addition to afford the β-(phenylseleno)vinyl p-toluenesulfonates 2-12, generally in high yield.The latter were formed preferentially by anti addition, but with poor regioselectivity, unless a strongly orienting group (e.g., phenyl) was present.Selenenyl sulfonate 1 was also unexpectedly produced via radical pathways by heating p-toluenesulfonic acid with AIBN in the presence of diphenyl diselenide, or from the pyrolysis of sulfinyl sulfone 15 with the diselenide.The regioisomeric adducts 3 and 4 were prepared from 1 and 1-decyne, and both underwent elimination with potassium tert-butoxide to afford the acetylenic selenide 19 initially, which isomerized to a 6:1 mixture of the propargylic and allenic selenides 20 and 21 upon further equilibration.A Fritsch-Buttenberg-Wiechell rearrangement is proposed for the elimination of 4.The syn elimination of the selenoxide of 4 required forcing conditions and afforded only ca. 20percent of the corresponding allenic sulfonate 22.The electrophile 1 induced the efficient cyclization of 5-hexen-1-ol and 4-pentenoic acid to the corresponding pyran 24 and lactone 25, respectively.It failed to cyclize alkynols, but afforded the lactones 28 and 29 from 4-pentynoic acid in low yield.
Free-Radical Additions of Diselenides to Dimethyl Acetylenedicarboxylate, Methyl Propiolate, and Dimethyl Maleate
Back, Thomas G.,Krishna, M. Vijaya
, p. 2533 - 2536 (2007/10/02)
The photolysis of diphenyl or dimesityl diselenide with dimethyl acetylenedicarboxylate or methyl propiolate resulted principally in the formation of the corresponding vicinal bisselenides 1a,b,2a,b, and 6a,b via a free-radical chain addition mechanism.Dimethyl maleate underwent a selenyl radical mediated isomerization to dimethyl fumarate when similarly photolyzed with diphenyl diselenide.
