Synthesis of carbamoyl azides via the Lossen rearrangement utilizing diphenyl phosphorazidate

A novel method was developed for the synthesis of carbamoyl azides from hydroxamic acids via the Lossen rearrangement using diphenyl phosphorazidate, which acts as both the activator and azide source to produce the azides via an isocyanate intermediate. Using this method, various hydroxamic acids were converted into the corresponding carbamoyl azides, enabling their preparation without the use of highly explosive reagents.(c) 2022 Elsevier Ltd. All rights reserved.

Automated summary

A novel method using diphenyl phosphorazidate was developed for the synthesis of carbamoyl azides from hydroxamic acids. This method avoids the use of highly explosive reagents and allows the conversion of various hydroxamic acids into the corresponding carbamoyl azides.