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Catalytic Reaction of Ethyl 2-Diazo-3-oxobutanoate with Alcohols


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Abstract

The effect of the structure of alcohols on their reaction with ethyl 2-diazo-3-oxobutanoate catalyzed by copper(II) trifluoromethanesulfonate has been studied. The corresponding ethyl 2-alkoxy-3-oxobutanoates were obtained in quantitative yield from primary alcohols. Introduction of a 1,3-dioxolane or 1,3-dioxane fragment into the alcohol molecule changes the reaction direction toward the formation of polyoxa macrocycles that are products of formal insertion of the diazo ester into the carbon–oxygen bond.

About the authors

G. N. Sakhabutdinova

Ufa State Petroleum Technological University

Email: graskildina444@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062

I. P. Baikova

Ufa Institute of Chemistry

Email: graskildina444@mail.ru
Russian Federation, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

G. Z. Raskil’dina

Ufa State Petroleum Technological University

Author for correspondence.
Email: graskildina444@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062

S. S. Zlotskii

Ufa State Petroleum Technological University

Email: graskildina444@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062

R. M. Sultanova

Ufa State Petroleum Technological University; Ufa Institute of Chemistry

Email: graskildina444@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062; pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

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