anti-Markovnikov addition of tellurium tetrachloride to trimethyl ethynyl silane |
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| Authors: | S.V. Amosova A.V. Martynov V.A. Shagun M.V. Musalov L.I. Larina L.B. Krivdin L.V. Zhilitskaya M.G. Voronkov |
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| Affiliation: | A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 1, Favorsky Street 664033, Russia |
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| Abstract: | An investigation of the TeCl4 interaction with trimethyl ethynyl silane 1 in CHCl3 has shown that anti-Markovnikov adduct [Z-1-(trimethylsilyl)-2-chlorovinyl]tellurium trichloride is formed as the only product. In time, it is hydrolyzed to give [Z-1-(trimethylsilyl)-2-chlorovinyl]tellurium (hydroxy) dichloride which, in turn, is dehydrated to afford bis[(2-chloro-1-trimethyl-silylvinyl)dichlorotellurium]oxide. These data revealed that the reaction studied was the first example of anti-Markovnikov syn-addition of TeCl4 to terminal acetylenes. A computed simulation of the TeCl4 interaction with ethynyl silane 1 in a gas state using PES method did not reveal dominating orientation of the addition but showed the conditions at which anti-Markovnikov addition can occur and which were probably met in carrying out the reaction in CHCl3. |
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| Keywords: | anti-Markovnikov addition Ethynyl silane Tellurium tetrachloride Multinuclear NMR spectroscopy Quantum-chemical calculations |
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