17436-90-7Relevant academic research and scientific papers
Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds
Shmakov, Mikhail M.,Bardin, Vadim V.,Prikhod'ko, Sergey A.,Adonin, Nicolay Yu
supporting information, (2019/08/20)
Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.
Transmetalation of Pentafluorophenylmercury Derivatives with Organylmagnesium Bromides
Bardin
, p. 1406 - 1408 (2019/08/21)
The reactions of pentafluorophenylmercury derivatives with organomagnesium compounds have been studied. The interaction of pentafluorophenylmercury chloride with RMgBr (R = Et, Ph) has afforded diphenyl- and diethylmercury or phenylmercury chloride, besides the expected product (C6F5HgR). The results have been explained by the transmetalation of C6F5HgR with the Grignard reagent, followed by the reaction of the resulting C6F5MgX (X = Br, C6F5) with pentafluorophenylmercury chloride. Transmetalation of (C6F5)2Hg with organylmagnesium bromides has led to the formation of C6F5MgX and R2Hg.
