Dioxazolone Explained

In organic chemistry, a dioxazolone is a cyclic carbonate incorporated into C₂NO₂ ring. It is an uncommon heterocyclic compound. They arise by the phosgenation of hydroxamic acids:

RC(O)NHOH + COCl₂ → RC=NO₂CO + 2 HClAlthough dioxazolones are often explosive, they are of interest as precursors to isocyanates:^[1]

RC=NO₂CO → R-N=C=O + CO₂

Dioxazolones have attracted attention as reagents for the preparation of amides.^[2]

References

1. 1,3,4-Dioxazol-2-ones: a potentially hazardous class of compounds. Middleton, William J.. Journal of Organic Chemistry. 1983. 48. 21. 3845–7. 10.1021/jo00169a059.
2. Comparative Catalytic Activity of Group 9 [Cp*MIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents. Park, Juhyeon . Chang, Sukbok . Angewandte Chemie International Edition in English. 2015. 54. 47. 14103–7. 10.1002/anie.201505820. 26404541.