Ethynyltri-n-butyltin reacts with the hydrogenation product of C2H5MgBr in THF, and in benzene containing traces of ether, with a cleavage of the C-Sn bond and the formation of acetylene, tri-n-butyltin hydride, vinyltri-n-butyltin, and a mixture of the cis- and trans-isomers of l,2-bis(tri-n-butylstannyl)-ethylene). In benzene this reaction proceeds with the liberation of acetylene and the formation of one of the l,2-bis(tri-n-butylstannyl)ethylene isomers.
Phenylpropiolic acid and styrene are formed when phenylacetylene is heated with the hydrogenation product of C2H5MgBr in THF and subsequent carbonation.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2557–2558, November, 1974.
The author expresses his deep gratitude to P. V. Petrovskii and I. D. Rubin for taking and deciphering the spectra.
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Savel'eva, I.S. Reactions of some unsaturated compounds with hydrogenation products of ethylmagnesium bromide. Russ Chem Bull 23, 2464–2465 (1974). https://doi.org/10.1007/BF00922132