88966-64-7Relevant articles and documents
REACTION OF p-TOLUENESULFONYL BROMIDE AND IODIDE WITH FUNCTIONAL DERIVATIVES OF VINYLACETYLENIC HYDROCARBONS
Kolosov, E. Yu.,Stadnichuk, M. D.,Nadezhina, L. S.
, p. 2006 - 2013 (2007/10/02)
Vinylacetylenic alcohols and chlorides add p-toluenesulfonyl bromide and iodide regiononselectively with the formation of acetylene and allene adducts.The proportion of the latter in the mixtures of isomers decreases in the transition from primary alcohols and chlorides to secondary and tertiary.Methyl vinylethynyl ketone, methyl vinylpropiolate, and diethylaminomethylvinylacetylene do not form addtion products under the same conditions.The relative reactivity of the investigated functional derivatives of the vinylacetylenes in the reactions of the acid bromide catalyz ed by copper(I) bromide decreases with increase in the conventional instability constant of the complexes of these unsaturated compounds with copper(I) ions.The conventional instability constants were determined by the polarographic method.In the noncatalyzed reactions with the acid iodide the relative reactivity of the vinylacetylene chlorides, alcohols, and methyl ethers is determined by the electron-donating character of the substituent R at the triple bond.
