Direct Observation of an Antihomoaromatic Bicyclooctadienyl Cation

[摘要] 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.

[学科分类] 化学（综合）