TY - JOUR
T1 - Reaction of phenylacetylene with sulfuric acid or sulfuric anhydride. Synthesis of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide
AU - Rogachev, V. O.
AU - Yusubov, M. S.
AU - Filimonov, V. D.
PY - 1999/3
Y1 - 1999/3
N2 - The influence of the reactant ratio and amount of dehydrating agent on the yield of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide in the reaction of phenylacetylene with sulfuric acid was studied. The product can decompose in aqueous acidic medium to give acetophenone. The highest yield of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide was obtained in the reaction of phenylacetylene with the SO3-dioxane complex or a solution of SO3 in chloroform-dioxane. Diphenylacetylene with SO3 does not form the corresponding β-sultone but undergoes oxidation to benzyl. Diphenylbutadiyne does not react with the SO3-dioxane complex.
AB - The influence of the reactant ratio and amount of dehydrating agent on the yield of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide in the reaction of phenylacetylene with sulfuric acid was studied. The product can decompose in aqueous acidic medium to give acetophenone. The highest yield of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide was obtained in the reaction of phenylacetylene with the SO3-dioxane complex or a solution of SO3 in chloroform-dioxane. Diphenylacetylene with SO3 does not form the corresponding β-sultone but undergoes oxidation to benzyl. Diphenylbutadiyne does not react with the SO3-dioxane complex.
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M3 - Article
AN - SCOPUS:0033089784
VL - 35
SP - 439
EP - 442
JO - Russian Journal of Organic Chemistry
JF - Russian Journal of Organic Chemistry
SN - 1070-4280
IS - 3
ER -