Dioxazolone

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 HCl

Although dioxazolones are often explosive, they are of interest as precursors to isocyanates:[1]

RC=NO2CO → RC=N=O + CO2

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

References
  1. Middleton, William J. (1983). "1,3,4-Dioxazol-2-ones: a potentially hazardous class of compounds". Journal of Organic Chemistry. 48: 3845-7. doi:10.1021/jo00169a059.
  2. Park, Juhyeon; Chang, Sukbok (2015). "Comparative Catalytic Activity of Group 9 [Cp*MIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents". Angewandte Chemie, International Edition. 54: 14103-14107. doi:10.1002/anie.201505820.CS1 maint: uses authors parameter (link)
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