Transannular Hydride Migration in  Pseudo‐Geminally  Substituted [2.2]Paracyclophanes: A Vinylogous Pinacol Rearrangement | Zendy

Birsa M. Lucian | Zendy; Jones Peter G. | Zendy; Hopf Henning | Zendy

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Transannular Hydride Migration in Pseudo‐Geminally Substituted [2.2]Paracyclophanes: A Vinylogous Pinacol Rearrangement

Author(s) -

Birsa M. Lucian,

Jones Peter G.,

Hopf Henning

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500093

Subject(s) - chemistry , hydride , pinacol , medicinal chemistry , stereochemistry , hydrogen , organic chemistry , catalysis

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)

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