Synthesis of 1, 3, 3-trinitroazetidine via the oxidative nitrolysis of Np-tosyl-3-azetidinone oxime

T Axenrod, C Watnick, H Yazdekhasti…

Index: Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P. R. Journal of Organic Chemistry, 1995 , vol. 60, # 7 p. 1959 - 1964

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Citation Number: 61

Abstract

The tert-butyldimethylsilyl ether of 1, 3-dibromo-2-propanol reacted with p- toluenesulfonamide in the presence of K&O3 to give the corresponding Np-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 Np-tosyl-3-azetidinol followed by oximation readily afforded Np-tosyl- ...