72256-09-8Relevant articles and documents
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.