104722-83-0Relevant academic research and scientific papers
Preparation of α-Arylseleno-substituted Zinc and Copper Organometallics and their Application in the Synthesis of α-Arylselenomethyl Ketones
Huang, Xian,Duan, De-Hui
, p. 396 - 397 (1998)
α-Arylseleno-substituted zinc and copper organometallics, prepared by zinc insertion into the carbon-chlorine bond of α-chloromethyl aryl selenides and with CuCN-2LiCl transmetallation to the corresponding copper reagents, react with acyl chlorides to give α-arylselenomethyl ketones based on the formation of a new carbon-carbon bond.
α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui,Pan, Zhangjin,Chen, Shuangshuang,Shen, Xuqian,Wu, Xiangmei
supporting information, p. 4305 - 4307 (2015/06/22)
Direct α-arylchalcogenation of acetone with diaryl dichalcogenides has been achieved by using a mixture of TBHP and DTBP oxidants at 120 °C without transition-metal catalyst via oxidative C(sp3)-H bond functionalization. The method exhibits good functional group tolerance and products were isolated in moderate to high yields.
Insertion of elemental selenium into zinc carbon bond and application in synthesis of α-selenocarbonyl compound
Huang, Xian,Xu, Xin-Hua
, p. 807 - 811 (2007/10/03)
Selenium inserted into the zinc carbon bond of alkyl and aryl zinc halides to form the corresponding the zinc alkyl and arylselnoates. They reacted in THF-HMPA with α-bromo carbonyl compounds to afford the α- selenocarbonyl compounds in high yields.
REACTION OF DIAZOMETHANE WITH SELENOESTERS PREPARATION OF α-(ALKYL- OR ARYLSELENO)METHYL KETONES AND METHYL KETONES
Back, Thomas G.,Kerr, Russell G.
, p. 4759 - 4764 (2007/10/02)
The reaction of diazomethane with a series of selenoesters 1 in the presence of CuI, CuSePh or Cu powder produced α-(alkyl- or arylseleno)methyl ketones 2 in yield of 41-65percent.Methyl ketones 3 and bis(arylseleno)methanes 9 or 14 were formed as by-products.The direct conversion of selenoesters to methyl ketones was accomplished in high yield by the usual reaction with diazomethane, followed by workup with HBr solution.The simultaneous copper-catalyzed reactions of selenoesters 1c and 1i with diazomethane resulted in crossover, with the formation of all four possible α-seleno ketones 2b, 2c, 2h and 2i.A non-concerted mechanism involving attack by the diazo compound upon the acyl carbon atom of an activated selenoester with the formation of a tetrahedral intermediate 11 has been suggested.The reaction of the selenothiocarbamate 4 with diazomethane resulted in 1,3-dipolar cycloaddition to afford 5 instead of insertion into the acyl-selenium bond.
