OXIDATIVE TRANSFORMATIONS OF LIGNANS - REACTIONS OF DIHYDROCUBEBIN AND A DERIVATIVE WITH DDQ

被引：35
|
作者：
PELTER, A [1 ]
WARD, RS [1 ]
VENKATESWARLU, R [1 ]
KAMAKSHI, C [1 ]
机构：
[1] ANDHRA UNIV,POSTGRAD EXTENS CTR,NUZVID 521201,INDIA
来源：
TETRAHEDRON | 1991年 / 47卷 / 07期
关键词：
D O I：
10.1016/S0040-4020(01)86384-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound (8) and the aryl tetralin (9), while with DDQ in trifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.
引用
收藏
页码：1275 / 1284
页数：10
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