74835-56-6Relevant academic research and scientific papers
Catalytic Electrophilic Thiocarbocyclization of Allenes
Jiang, Quanbin,Li, Huimin,Zhao, Xiaodan
supporting information, p. 8777 - 8782 (2021/11/17)
An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence o
Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions
Ting, Chun-Ming,Hsu, Yi-Ling,Liu, Rai-Shung
, p. 6577 - 6579 (2012/07/31)
We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.
Umpolung of carbon-sulfur bonds. Novel synthesis of substituted allenes from propargylic dithioacetals
Tseng, Hsian-Rong,Lee, Chin-Fa,Yang, Lian-Ming,Luh, Tien-Yau
, p. 8582 - 8587 (2007/10/03)
Umpolung of the carbon-sulfur bonds can be achieved by treatment of propargylic dithioacetals 1 with organocuprates. The organocopper intermediates 3 gave the corresponding allenyl thioethers 4 upon protonolysis. When alkyl halides were used, propargylic thioethers 5 were obtained exclusively. Transmetalation of organocopper intermediates 3 with ZnBr2 followed by Pd(PPh3)4-catalyzed coupling with vinylic or aryl halides afforded the corresponding allenyl thioethers 4. Either 4 or 5 reacted with Grignard reagents in the presence of NiCl2(dppf) to yield the corresponding allenes 9 or 10, respectively. The overall reaction can be considered to use 1 as allene-1,3-zwitterion synthons. The relative reactivities of a propargylic ether versus a propargylic dithioacetal toward an organocopper reagent were compared. The sulfur moiety apparently has higher reactivity toward the copper reagent.
Reaction of Propargylic Substrates wiht Organocopper Species. Synthetic Aspects
Macdonald, Timothy L.,Reagan, David R.
, p. 4740 - 4747 (2007/10/02)
The reaction of propargylic substrates with organocopper species can yield two major products, a substituted allene or a new acetylene.This paper is a study of the factors which influence the distribution of these products in this displacement (e.g., 1-->
