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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 07期

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

页码：1959 / 1964

页数：6

共 50 条

[1]

ALSTER J, 1990, NATO ADV SCI I C-MAT, V309, P641

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