| Abstract
| - The bromination of 5.8-diacetoxy-1,4-dihydro-1,4-ethanonaphthalenewas reported several yearsago to yield a single stereospecificly formed dibromide. Givenrelated cases from the literature,the result was interpreted as indicating a significant interactionbetween the aryl and olefinπ-electron systems. This paper reports an ab initio study of themechanism of the bromination ofbenzobicyclooctadiene. It is proposed that the stereochemistry isbest accommodated by anasynchronous concerted electrophilic addition of bromine across carbons1 and 3, and that it proceedsvia an ion pair transition structure in which the Wagner−Meerweinportion of the reaction hasalready occurred. All final results were calculated at theBecke3LYP/6-31G* level.
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