Practical synthesis of 9-methylthio-7,8-nido-carborane [9-MeS-7,8-C2B9H11]-. Some evidences of BH•••X hydride-halogen bonds in 9-XCH2(Me)S-7,8-C2B9H11 (X = Cl, Br, I)

被引:29
作者
Anufriev, Sergey A. [1 ]
Sivaev, Igor B. [1 ]
Suponitsky, Kyrill Yu. [1 ]
Bregadze, Vladimir I. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov Str 28, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
nido-Carborane; Sulfonium derivatives; B-H center dot center dot center dot X hydride-halogen interactions; Synthesis; NMR spectroscopy; ALKALI-METAL AMIDOBORANES; REDOX CONTROL; HYDROGEN; COMPLEXES; CRYSTAL; DERIVATIVES; TRANSITION; CHEMISTRY; BIS(DICARBOLLIDES); FLUORESCENCE;
D O I
10.1016/j.jorganchem.2017.03.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Convenient method of synthesis of 9-methylthio-7,8-nido-carborane [9-MeS-7,8-C2B9H11](-) based on demethylation of the dimethylsulfonium derivative 9-Me2S-7,8-C2B9H11 with sodium amide in toluene was developed. A series of alkylmethylsulfonium derivatives of nido-carborane containing heteroatoms with lone electron pairs at alpha-position of alkyl were prepared 9-XCH2(Me)S-7,8-C2B9H11 (X = Cl, Br, I, OMe) by alkylation of [9-MeS-7,8-C2B9H11](-). The B-11 NMR spectra of these compounds demonstrate splitting signals corresponding to B(5) and B(10) atoms that can be explained by the weak intramolecular B-H center dot center dot center dot X interactions in the diastereomers containing alkyl groups directed downwards and upwards relatively to the nido-carborane pentagonal face. The existence of such interactions was supported by quantum chemical calculations. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:315 / 323
页数:9
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