Synthesis of 10-methylsulfide and 10-alkylmethylsulfonium nido-carborane derivatives. B-H…π Interactions between the B-H-B hydrogen and alkyne group in 10-RC≡CCH2S(Me)-7,8-C2B9H11статья
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Дата последнего поиска статьи во внешних источниках: 10 февраля 2018 г.
Аннотация: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 Å. This is the first example of B–H···π(C≡C) hydrogen bonding.