Thermolysis of 2-methoxy-2,5,5-trimethyl-3-1,3,4-oxadiazoline

The principal product of gas phase thermal decomposition of 2-methoxy-2,5,5-trimethyl-Δ 3 -1,3,4-oxadiazoline (methoxyoxa-diazoline) was found to be 1-methoxy-1-[(1-methylethenyl)oxy]-ethane (vinyl ether). This arises from a selective 1,4-hydrogen shift in the carbonyl ylide intermediate. Fragmentation of the carbonyl ylide is the dominant process in the solution thermolysis of methoxyoxadiazoline. The phase and temperature dependence of this …