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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 3, Number 2
BKCSDE 3(2)
February 20, 1982 

 
Title
Direct Observation of an Antihomoaromatic Bicyclooctadienyl Cation
Author
Jung-Hyu Shin
Keywords
Abstract
The question of the bicyclohomoaromatic stabilization and destabilization is examined. The chemistry of bicyclo(3.2.1)octa-3,6-dienide anion has been studied on order to test these concepts. The bicyclooctadienide anion is shown to be stable delocalized ion which undergoes a facile proton-deuterium exchange reaction. The solvolysis of bicyclo(3.2.1)octa-3,6-dienyl p-nitrobenzoate is much slower than the monoene analog. We have made direct observation of the bicyclooctadienyl and octenyl cations by 19F-nmr spectroscopy, and were able to demonstrate that the bicyclooctadienyl cation was bishomoantiaromatic.
Page
66 - 70
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