94683-14-4

Upstream product

• 154010-93-2 3-(p-toluenesufonamido)propane-2-ol-1-(p-toluenesulfonate) 
• 70-55-3 toluene-4-sulfonamide 
• 106-89-8 epichlorohydrin 

Downstream Products

• 95555-05-8 3,7-bis-(toluene-4-sulfonyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]nonan-1-ol 
• 202211-14-1 3,7-bis(4-methylbenzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol 
• 160624-80-6 1,5-ditosyl-1,5-diazocane-3,7-dione 

Relevant academic research and scientific papers

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-toluenesulfonate) 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.

Synthesis of 1,3,3-Trinitroazetidine

The t-butyldimethylsilyl ether of 3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) on treatment with LiH undergoes ring closure to the corresponding azetidine which is readily converted to N-tosyl-3-azetidinone oxime.By oxidative nitrolysis the latter affords 1,3,3-trinitroazetidine.