Journal of Organic Chemistry p. 1959 - 1964 (1995)
Update date:2022-08-04
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Axenrod, T.
Watnick, C.
Yazdekhasti, H.
Dave, P. R.
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.
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