DO DEPROTONATED AMIDOXIMES UNDERGO THE TIEMANN REARRANGEMENT IN THE GAS-PHASE

被引：5

作者：

ADAMS, GW ^{[1
]}

BOWIE, JH ^{[1
]}

HAYES, RN ^{[1
]}

GROSS, ML ^{[1
]}

机构：

[1] UNIV NEBRASKA,DEPT CHEM,LINCOLN,NE 68588

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1992年 / 06期

关键词：

D O I：

10.1039/p29920000897

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Tiemann rearrangement in the condensed phase involves base-catalysed transformation of suitably substituted amidoximes to ureas, e.g. [GRAPHICS] In contrast, deprotonated amidoximes, in the gas phase, undergo only minor reaction through Tiemann intermediates. Instead, they decompose by loss of hydroxylamine, e.g. -NHC(Me)=NOH <-- --> NH=C(Me) - NBAROH --> [(MeCN) -NHOH] --> -CH2CN + NH2OH a process substantiated by N-14 and H-2 labelling and product-ion studies.

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页码：897 / 901

页数：5

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