Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl5-Mg and NbCl5-Mg Reagent System

Abstract

: A regioselective method for the preparation of p -tolyl-substituted alkanes based on the reaction of dialkyl-substituted alkynes with 4 equiv. of TaCl 5 or NbCl 5 in the presence of stoichiometric amounts of metallic magnesium in toluene solution. It was found that the reaction of 5-decyne with the TaCl 5 - M reagent system (where М = Mg, Zn, Fe, Sm, Al, Mn) in a toluene sol u-tion is accompanied by the selective formation of 1-(decan-5-yl)-4-methylbenzene in a high yield (79 – 90%). The effect of solvents on the selectivity of the conversion of 5-decyne under the action of the TaCl 5 -Mg reagent system has been studied.