Abstract
The entitled reactions were investigated by molecular orbital calculations. Methyl isocyanate and ethylene oxide were adopted as model reactants. The product, 2-oxazolidone, may be produced through a dual SN2 reaction, where a catalyst base (e.g. Cl-) will attack the ethylene-oxide carbon nucleophilically. An isocyanurate is generated by the stepwise association of three isocyanate molecules, where one of them has been linked with the base from the initial stage. The 6-membered-ring isocyanurate is isomerized stepwise and converted into the corresponding isocyanate and 2-oxazolidone. A tetrahedral-type complex from the isocyanurate and base-catalyzed ethylene oxide is the key intermediate for the isomerization.
