AMINOBENZANNULATION VIA PHOTOCYCLIZATION REACTIONS OF CHROMIUM DIENYL(AMINO)CARBENE COMPLEXES - SYNTHESIS OF O-AMINO AROMATIC ALCOHOLS

被引:60
作者
MERLIC, CA
XU, DQ
GLADSTONE, BG
机构
[1] Department of Chemistry and Biochemistry, University of California, Los Angeles
关键词
D O I
10.1021/jo00055a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photolysis of chromium dienyl(amino)carbene complexes is demonstrated to produce o-amino aromatic alcohols. The reaction is proposed to preceed via a chromium-complexed photogenerated dienylketene which undergoes subsequent electrocyclization and aromatization. These reactions are sensitive to the electronic nature of the amino substituent on the carbene carbon and can be tuned by variation in substituents. In particular, the ability to facilitate photolytic ketene generation by employing (acylamino)carbene complexes is illustrated. In addition, new methods of conversion of alkoxycarbene complexes to aminocarbene complexes are described.
引用
收藏
页码:538 / 545
页数:8
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