Synthesis and Reactions of the First Examples of the 1,5,2,4-Dioxadiazine Ring System: 2,4-Dialkyl-2H-1,5,2,4-dioxadiazine-3,6(4H)-diones

Article abstract of DOI:10.1021/jo00367a019

The synthesis and selected reactions of 2,4-di-tert-butyl- and 2,4-bis(1,1,3,3-tetramethylbutyl)-2H-1,5,2,4-dioxadiazine-3,6(4H)-dione are described.Phosgenation of N-tert-alkylhydroxylamines gives the carbonate compounds 2 which upon further phosgenation afford the dioxadiazines 1.Acidified silica gel is required for their purification.The dioxadiazines decompose upon heating to give the corresponding nitroso compound and the isocyanate.The ring is rapidly cleaved by nucleophiles such as dimethylamine.