Transannular hydride migration in pseudo-geminally substituted [2.2]paracyclophanes:: A vinylogous pinacol rearrangement

被引：16
|
作者：
Birsa, ML
Jones, PG
Hopf, H
机构：
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan & Analyt Chem, D-38106 Braunschweig, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期
关键词：
2.2]paracyclophanes; pinacol rearrangement; hydride transfer;
D O I：
10.1002/ejoc.200500093
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A vinylogous pinacol-pinacolone rearrangement is reported that takes place although the two hydroxyl groups are formally separated by seven bonds. It involves a transannular hydride shift that occurs between the benzylic positions of the pseudo-geminally substituted [2.2]paracyclophanes 1a-c, 7, 8 and 9. Under mild acidic conditions the corresponding pseudo-geminally substituted cyclic ethers were established as stable intermediates. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码：3263 / 3270
页数：8
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