100618-58-4Relevant academic research and scientific papers
CHLOROARYLATION OF ALLYL ALCOHOL AND ITS ETHERS AND ESTERS
Karpyak, V. V.,Obushak, N. D.,Ganushchak, N. I.
, p. 1692 - 1699 (2007/10/02)
Allyl alcohol, allyl formate, allyl acetate, allyl propionate, allyl chloroacetate, allyl difluoroacetate and allyl methyl, allyl ethyl, diallyl, and allyl phenyl ethers react with arenediazonium chlorides in the presence of copper chloride with the formation of the products from addition of the aryl group and chlorine at the double bond of the olefin.It was established that the reaction of the synthesized esters with secondary amines takes place through the formation of epoxides, followed by opening of the oxirane ring by the amine according to the Krasuskii rule.The reaction of 1-formyloxy-2-chloro-3-phenylpropane with potassium hydroxide in ethanol had the same regioselectiviy and gave 1-ethoxy-3-phenyl-2-propanol.The quaternary ammonium salts of the obtained amino alcohols were synthesized.The action of potassium 4-nitrophenolate on 1-acyloxy-2-chloro-3-arylpropanes gave the products from formal substitution of the ester group by the 4-nitrophenoxyl group.
