131619-35-7Relevant academic research and scientific papers
Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones
Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong
supporting information, p. 14195 - 14201 (2021/09/20)
A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.
Peterson Olefination Reaction Using (Trimethylgermyl)acetate. Stereoselective Synthesis of (E)-2-Alkenoic Acid Esters
Inoue, Sumie,Sato, Yoshiro
, p. 347 - 352 (2007/10/02)
Peterson-type reaction of (trimethylgermyl)acetates 1 with aldehydes and ketones 2 gave stereoselectively (E)-2-alkenoic acid esters (E)-4 after stirring at -78 deg C and warming to room temperature.High yields of the reaction intermediates threo- and erythro-3-hydroxy-2-(trimethylgermyl)alkanoic acid esters 3 were obtained when the reaction was quenched at -78 deg C.The paths for conversion of threo-3 and erythro-3 to (E)-4 are discussed.
