79354-25-9Relevant academic research and scientific papers
REACTION OF METHYL ETHERS OF VINYLACETYLENIC ALCOHOLS WITH p-TOLUENESULFONYL BROMIDE AND IODIDE
Kolosov, E. Yu.,Stadnichuk, M. D.
, p. 1047 - 1053 (2007/10/02)
The direction of the addition of p-toluenesulfonyl bromide (in the presence of catalytic amounts of cuprous bromide) and p-toluenesulfonyl iodide to ethers of vinylacetylenic alcohols is a factor of the ether structure: 5-methoxy-1-penten-3-yne adds these reagents independently of the nature of the halide exclusively in the 1,4 positions, 5-methoxy-5-methyl-1-hexen-3-yne adds to the double bond, while 5-methoxy-1-hexen-3-yne adds with the formation of adducts at the double bond and at the 1,4 positions.In the reaction studied, the ethers are less reactive than the analogous vinylacetylenic hydrocarbons and their relative reactivity decreases in the series: 5-methoxy-1-penten-3-yne > 5-methoxy-1-hexen-3-yne > 5-methoxy-5-methyl-1-hexen-3-yne.
