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

被引:53
作者
AXENROD, T [1 ]
WATNICK, C [1 ]
YAZDEKHASTI, H [1 ]
DAVE, PR [1 ]
机构
[1] GEOCENTERS INC, ARDEC, LAKE HOPATCONG, NJ 07849 USA
关键词
D O I
10.1021/jo00112a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
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页码:1959 / 1964
页数:6
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