Abstract
Hydroalkoxylation of alkynes by a nitroxyl containing alcohol, 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl: synthesis of spin-labeled enol ethers
Highlights
Stable free radicals of nitroxyl type are under ever-increasing studies due to their importance in a variety of developing areas of modern science and technology, in design of high-tech materials.[1,2,3] Among such species, 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) and its congeners are of special interest
To develop an efficient synthesis of 4-vinyloxy-TEMPO, the reaction of 4-hydroxy-TEMPO (1) with acetylene in the KОН/DMSO system was studied under atmospheric pressure
A general and efficient methodology for the synthesis of enol ethers bearing paramagnetic TEMPO moieties has been developed using the KOH/DMSO-catalyzed regioselective hydroalkoxylation of diverse alkynes by available 4-hydroxy-TEMPO. This reaction readily proceeds under environmentally benign transition metal free conditions at atmospheric pressure and mild heating
Summary
Stable free radicals of nitroxyl type are under ever-increasing studies due to their importance in a variety of developing areas of modern science and technology, in design of high-tech materials.[1,2,3] Among such species, 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) and its congeners are of special interest. In view of these data, and the earlier result of predominant reduction of 4-hydroxy-TEMPO during its vinylation by acetylene in the KOH/DMSO system, it remains unclear whether efficient base-catalyzed hydroalkoxylation of nitroxyl-containing alcohols with alkynes is possible This issue is of fundamental importance to the question of the mechanism of nucleophilic addition of alkoxide to the C≡C triple bond
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