T. Tsuchida, K. Koyama, M. Mitani
Apr 1, 1980
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Ethyl azidoformate (1) reacts rapidly with morpholine to give morpholinium azide and 4-(ethoxycarbonyl)morpholine in good yields. With 4-methylmorpholine (3), however, the azide 1 reacts at 115 °C with evolution of nitrogen to give formal nitrene-insertion products, 4-methyl-3-(ethoxycarbonylamino)morpholine and 4-(ethoxycarbonylaminomethyl)morpholine. There has not been found any product which might arise from the nitrene–insertion into C–H bond adjacent of oxygen of 3. These results can be accounted for on the basis of the n-donor abilities of heteroatoms, O and N.