Reaction of phenylacetylene with sulfuric acid or sulfuric anhydride. Synthesis of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide

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Abstract

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.

Original languageEnglish
Pages (from-to)439-442
Number of pages4
JournalRussian Journal of Organic Chemistry
Volume35
Issue number3
Publication statusPublished - Mar 1999

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Oxathiins
Anhydrides
Chloroform
Oxidation
diphenyl
1,4-dioxane
sulfuric acid
phenylacetylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Reaction of phenylacetylene with sulfuric acid or sulfuric anhydride. Synthesis of 4,6-diphenyl-1,2-oxathiin 2,2-dioxide",
abstract = "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.",
author = "Rogachev, {V. O.} and Yusubov, {M. S.} and Filimonov, {V. D.}",
year = "1999",
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pages = "439--442",
journal = "Russian Journal of Organic Chemistry",
issn = "1070-4280",
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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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