ORTHO-ARYLATION OF 3,5-DI-TERT-BUTYLPHENOL WITH ARYLLEAD(IV) DERIVATIVES - A FACILE SYNTHESIS OF STERICALLY HINDERED PHENOLS

被引：20
作者：
BARTON, DHR
DONNELLY, DMX
GUIRY, PJ
FINET, JP
机构：
[1] NATL UNIV IRELAND UNIV COLL DUBLIN,DEPT CHEM,DUBLIN 4,IRELAND
[2] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843
[3] FAC SCI & TECH ST JEROME,F-13397 MARSEILLE 20,FRANCE
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 20期
关键词：
D O I：
10.1039/p19940002921
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of aryllead(IV) triacetates with 3,5-di-tert-butylphenol 1 has been shown to yield very hindered 2-aryl-3,5-di-tert-butylphenols and 2,6-diaryl-3,5-di-tert-butylphenols such as 15 and 16. The mechanism of this arylation reaction with aryllead(IV) derivatives is discussed. A free radical pathway has been excluded. The favoured pathway must involve the occurrence of covalent aryl(aryloxy)lead (IV) diacetate intermediates, although they have not been detected. The required aryl cation behaviour of the lead reagents is supported by C-13 NMR spectroscopic studies on aryllead triacetates.
引用
收藏
页码：2921 / 2926
页数：6
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