SYNTHESIS OF 1,3,3-TRINITROAZETIDINE VIA THE OXIDATIVE NITROLYSIS OF N-P-TOSYL-3-AZETIDINONE OXIME

The tert-butyldimethylsilyl ether of 1,3-dibromo-2-propanol reacted with p-toluenesulfonamide in the presence of K2CO3 to give the corresponding N-p-tosyl-3-azetidinol. The same azetidinol was obtained when the similarly silyl-protected 3-(p-toluenesulfonamido)propan-2-ol 1-(p-toluene-sulfonate) was treated with LiH. Desilylation and oxidation of the N-p-tosyl-3-azetidinol followed by oximation readily afforded N-p-tosyl-3-azetidinone oxime. Oxidative nitrolysis of the latter intermediate delivered 1,3,3-trinitroazetidine through a new sequence of reactions.