2,3-DIMETHOXYPERHYDRO-1,4,2,3-DIOXADIAZINE - SYNTHESIS, CONFORMATION,AND CONVERSION TO 1-(2-HYDROXYETHOXY)-2-METHOXYDIAZENE-1-OXIDE - CRYSTAL-STRUCTURE OF -NITROBENZOYLOXY)-ETHOXY]-2-METHOXYDIAZENE-1-OXIDE

The oxidation of 1,2-bis(methoxyaminooxy)ethane (3) with PbO2 afforded 2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine (4) in the form of the 55: 45 mixture of the trans-4ee- and cis-4 isomers. The barrier of the rin g conversion (DELTAG238 not-equal = 11.3 kcal/mole) of the cis-4 isome r was determined by the method of C-13 NMR. The regio- and stereospeci fic stereoelectronically controlled reaction of (4) with para-nitroben zoic acid gives the equimolar mixture of methyl para-nitrobenzoate and the 1,2-dialkoxydiazene oxide (5), the structure of which, and the (E )-configuration, were shown by the x-ray structural data of its acylat ion product - the diazene oxide (6).