✦ LIBER ✦
Transannular Hydride Migration in Pseudo-Geminally Substituted [2.2]Paracyclophanes: A Vinylogous Pinacol Rearrangement
✍ Scribed by M. Lucian Birsa; Peter G. Jones; Henning Hopf
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 145 KB
- Volume
- 2005
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)