72256-09-8Relevant academic research and scientific papers
Shelf-Stable (E)- A nd (Z)-Vinyl-λ3-chlorane: A Stereospecific Hyper-vinylating Agent
Kanazawa, Junichiro,Miyamoto, Kazunori,Takagi, Taisei,Uchiyama, Masanobu,Watanabe, Yuichiro
supporting information, p. 3469 - 3473 (2020/04/30)
We report the first stereoselective synthesis of stable (E)- A nd (Z)-β-chlorovinyl-λ3-chlorane via direct mesitylation of 1,2-dichloroethylene with mesityldiazonium tetrakis(pentafluorophenyl)borate under mild reaction conditions. The structure of the (E)-vinyl-λ3-chlorane was established by single-crystal X-ray analysis. Because of the enormously high leaving group ability of the aryl-λ3-chloranyl group, vinyl-λ3-chloranes undergo not only SNVσ-type reaction with extremely weak nucleophiles such as perfluoroalkanesulfonate, iodobenzene, and aromatic hydrocarbons but also coupling with phenylcopper(I) species.
REACTIONS OF CHLORINE MONOFLUORIDE. V. REGIOSPECIFICITY AND STEREOCHEMISTRY IN THE ADDITION OF CHLORINE MONOFLUORIDE TO E- AND Z-1-BROMO-2-CHLOROETHYLENES AND 1,2-DIBROMOETHYLENES
Boguslavskaya, L. S.,Ternovskoi, L. A.
, p. 1647 - 1652 (2007/10/02)
The chlorofluorination of Z- and E-1-bromo-2-chloroethylenes and 1,2-dibromoethylenes with hexachloromelamine in anhydrous hydrogen fluoride and with chlorine monofluoride in Freon 113 was investigated.The addition of ClF at the multiple bond of alkenes is nonregiospecific and nonstereospecific.The direction and stereochemistry of addition depend on the reagent, the substrates, and the medium.The mechanism of chlorofluorination was examined, and it was shown that in both media the reaction takes place with the participation of chloronium and bromonium carbocationic intermediates.
