82490-61-7Relevant articles and documents
Synthesis of 10-Methylsulfide and 10-Alkylmethylsulfonium nido-Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10-RC≡CCH2S(Me)-7,8-C2B9H11
Anufriev, Sergey A.,Sivaev, Igor B.,Suponitsky, Kyrill Yu.,Godovikov, Ivan A.,Bregadze, Vladimir I.
, p. 4436 - 4443 (2017)
The 10-dimethylsulfonium derivative of nido-carborane 10-Me2S-7,8-C2B9H11 was prepared by reaction of the protonated form of nido-carborane with dimethylsulfide in toluene. Its partial demethylation with sodium amide in toluene gave the corresponding 10-methylsulfide derivative [10-MeS-7,8-C2B9H11]–. This 10-methylsulfide derivative was alkylated with various alkylating agents to produce a series of 10-alkylmethylsulfonium derivatives 10-R(Me)S-7,8-C2B9H11 (R = Et, Pr, Bu, CH2CH=CH2, CH2Ph, CH2C≡CH, CH2C≡CPh, CH2C≡CSiMe3). The 11B NMR spectra of the latter three compounds containing an acetylene group demonstrate unusually strong signal splitting that can be explained by strong intramolecular B–H···π(C≡C) interactions. The existence of such interactions in the solid state was supported by the X-ray crystal structure of 10-HC≡CCH2(Me)S-7,8-C2B9H11 with a short B–H···C(C≡C) distance of 2.658 ?. This is the first example of B–H···π(C≡C) hydrogen bonding.
Intercepting the Banert cascade with nucleophilic fluorine: Direct access to α-fluorinated: N H-1,2,3-triazoles
Alexander,Kevorkian,Topczewski
supporting information, p. 5024 - 5027 (2021/05/28)
The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reacti
Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride
Hammond, Gerald B.,Li, Wangbing,Lu, Zhichao,Xu, Bo
supporting information, p. 9640 - 9644 (2021/12/14)
An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.
