Addition of arenesulfenyl chlorides to quadricyclene

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Title: Addition of arenesulfenyl chlorides to quadricyclene
Author: Niger, Robert J.
Abstract: The addition of arenesulfenyl chlorides to quadricyclene has been investigated. These reactions are rapid, exothermic and yield primairly three isomers. Two of the isomers (type I and type II structures) have the norbornene and nortricyclene carbon skeletons respectively. The structure of the nortricyclene isomer has been thoroughly established with a wide variety of techniques including 2D NMR. It has been found that a bridged sulfonium ion is not an important product precurser in these electrophilic addition reactions. In a attempt to force the formation of a bridged ion, preliminary studies using arenesulfenyl chlorides in which the aromatic ring contains electron-donating groups have been carried out. The results of these reactions suggest that the amount of bridged ion precurser present is minor at best. Studies of the ratio of isomers I to I I to I 1 1 reveal complex patterns, and suggest conclusions about kinetic control. In summary, a significant niche in mechanistic theory has been established, but more exploration would be necessary to induce bridged ion formation and to completely establish all the caveats of this process.
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Date: 1992-08

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