Addition, Elimination, and Rearrangement Reactions of Cyclopropyl-Substituted Nitrenium Ions: A Computational and Experimental Investigation
Donald Hong,
Daniel Falvey
Abstract:Two cyclopropyl substituted nitrenium ions were generated through photolysis of their corresponding N-aminopyridinium ion photoprecursors. In the case of N-biphenyl-N-cyclopropyl nitrenium ion (5). Stable products are derived from a combination of cyclopropyl ring expansion, forming N-biphenylazetium ion, and ethylene elimination, forming biphenylisonitrilium ion. When present in high concentrations, methanol can add to the cyclopropyl ring forming N-3-methoxypropyl-N-biphenyl iminium ion. In contrast, the onl… Show more
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