Collect. Czech. Chem. Commun. 2006, 71, 1517-1524

Electrochemical Oxidation of But-2-yne-1,4-diol

Jaromír Hlavatýa,* and Martin Štíchab

a J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 182 23 Prague 8, Czech Republic
b Department of Organic Chemistry, Faculty of Science, Charles University, Albertov 2030, 128 41 Prague 2, Czech Republic


But-2-yne-1,4-diol (1) was electrochemically oxidized on glassy carbon anode in a dry THF solution containing a quaternary ammonium salt, in an undivided cell giving di(1,3-dioxepan-2-yl)ethyne (5) in 80% yield. The electrochemically generated dialdehyde intermediate is assumedly acetalized in a fast reaction with THF. Dimerized product 6 was isolated in 85% yield after electrooxidation of diol 1 in dry 1,2-dimethoxyethane under similar conditions.

Keywords: Anhydrous electrolytes; But-2-yne-1,4-dial diacetal; But-2-yne-1,4-diol; Galvanostatic preparative electrooxidation; Di(1,3-dioxepan-2-yl)ethyne.

References: 12 live references.