Synthesis and Properties of 2,3-Dimethoxy-1,4,2,3-dioxadiazinane and Dialkoxydiazene Oxides

The oxidation of 1,2-bis(methoxyaminooxy)ethane 1 with PbO₂ results in the formation of 2,3-dimetboxy-1,4,2,3-dioxadiazinane 2 as a mixture of trans- and cis-isomers (55:45), the regio- and stereo-specific reaction of which with p-nitrobenzoic acid gives (E)-dialkoxydiazene oxide 3 and methyl p-nitrobenzoate.