RELATIVELY STABLE N-BENZHYDRYLKETENE AND N-BENZYLDIARYLKETENE IMINES AND THEIR CONVERSION TO CYANODIARYLMETHANES VIA AN ISOLABLE RADICAL

被引:28
作者
CLARKE, LF [1 ]
HEGARTY, AF [1 ]
ONEILL, P [1 ]
机构
[1] NATL UNIV IRELAND UNIV COLL DUBLIN,DEPT CHEM,DUBLIN 4,IRELAND
关键词
D O I
10.1021/jo00027a062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthetic route to the sterically hindered ketene imines N-benzyl- and N-benzylhydrylbis(pentamethylphenyl)ketene imines 8 from dipentamethylphenyl ketene 6 is described. The thermal stability of these ketene imines is in marked contrast to the diphenylketene imine analogues which rearrange rapidly to C-tri-substituted nitriles. On heating 8b is converted to the relatively stable free radical 13 which can be reduced to the nitrile 10 in a variety of solvents. These radicals are proposed intermediates in the ketene imine-nitrile rearrangement, and the mechanism of this reaction is considered in in terms of these results.
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页码:362 / 366
页数:5
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