154010-93-2

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 154010-94-3 3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) t-butyldimethylsilyl ether 
• 94683-14-4 1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol 
• 76543-27-6 1-(p-toluenesulfonyl) azetidin-3-one 
• 154010-97-6 3-oximino-1-(p-toluenesulfonyl) azetidine 
• 154010-96-5 1-(p-Toluenesulfonyl)azetidin-3-ol 
• 154010-95-4 1-(p-Toluenesulfonyl)-3-(tert-butyldimethylsiloxy)azetidine 

Relevant academic research and scientific papers

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.

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.