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A new method for the synthesis of tetraalkyl-substituted buta-1,3-dienes using TaCl5-catalyzed reaction of dialkyl-substituted alkynes with EtAlCl2 in the presence of metallic magnesium.
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1  Institute of Petrochemistry and Catalysis of Russian Academy of Sciences
Academic Editor: Julio A. Seijas

https://doi.org/10.3390/ecsoc-25-11699 (registering DOI)
Abstract:

For the first time, regio- and stereoselective synthesis of tetraalkyl-substituted buta-1,3-dienes was carried out using the reaction of dialkyl-substituted alkynes with EtAlCl2 and metallic magnesium in the presence of catalytic amounts of tantalum (V) chloride in a toluene solution. The effect of the nature of the solvent and temperature on the process of oxidative coupling of molecules of disubstituted alkynes on low-valent tantalum has been studied. A scheme is proposed for the catalytic conversion of disubstituted alkynes to buta-1,3-dienes under the conditions of organoaluminum synthesis. It was found that the reaction of in situ obtained metallocyclopentadienes with methanesulfonyl chloride leads to the selective formation of tetraalkyl-substituted 1,4-dichlorobuta-1,3-dienes.

Keywords: Alkynes; tantalum(V) chloride; metallic magnesium; diethylaluminum chloride; buta-1,3-dienes

 
 
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