6533b7d7fe1ef96bd1268cc0

RESEARCH PRODUCT

Electron-transfer reduction of selected alcohols with alkalide K−, K+(15-crown-5)2 via organometallic intermediates

Józef RzepaHolger FreyZbigniew GrobelnyAdalbert MaerckerJanusz KasperczykStanisław KrompiecAndrzej Stolarzewicz

subject

chemistry.chemical_classificationPotassium methoxideAlkalidePotassiumOrganic Chemistrychemistry.chemical_elementVinyl etherBiochemistryPotassium oxideInorganic Chemistrychemistry.chemical_compoundchemistry15-Crown-5Polymer chemistryMaterials ChemistrymedicineOrganic chemistryMethanolPhysical and Theoretical ChemistryCrown ethermedicine.drug

description

Abstract The course of the reaction of alkalide K − , K + (15-crown-5) 2 1 with selected alcohols depends on the kind of alcohol and the mode of substrate delivery. In the case of methanol, potassium methoxide formed initially undergoes destruction at the excess of 1 . It results in potassium oxide and methylpotassium. The latter opens the crown ether ring giving potassium tetraethylene glycoxide vinyl ether and methane. A similar course of the process is observed for propanol. Potassium glycidoxide is the main product formed in the reaction of 1 with glycidol. Its oxirane ring is opened at the excess of 1 . Organopotassium alkoxides, i.e., potassium potassiomethoxide and dipotassium potassiopropane-1,2-dioxide are intermediate products of this reaction. They react then with the crown ether. Potassium methoxide, potassium enolate of acetaldehyde, dipotassium propane-1,2-dioxide and potassium tetraethylene glycoxide vinyl ether are the final products of this process.

yearjournalcountryeditionlanguage
2004-07-01Journal of Organometallic Chemistry
https://doi.org/10.1016/j.jorganchem.2004.04.026