Novel syntheses of 1,3,3‐trinitroazetidine

Abstract Alternative methods for the synthesis of 1,3,3‐trinitroazetidine (TNAZ) from epichlorohydrin, and benzhydrylamine have been developed. These approaches employ N ‐sulfonyl‐3‐(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures. Parallel methods employing N ‐benzhydryl‐ and N ‐benzyl‐3‐(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ.