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.

Original language	English
Pages (from-to)	439-442
Number of pages	4
Journal	Russian Journal of Organic Chemistry
Volume	35
Issue number	3
Publication status	Published - Mar 1999

ASJC Scopus subject areas

Organic Chemistry

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@article{c3d797e0995e45ceaee13593632acd5d,

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",

month = mar,

language = "English",

volume = "35",

pages = "439--442",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "Maik Nauka-Interperiodica Publishing",

number = "3",

}

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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VL - 35

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EP - 442

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

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