Premium
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
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)