Abstract
The aminium radicals generated from the photolysis of N-nitroso-endo-2-methylamino-methylbicyclo[2.2.1]hept-5-en and N-nitroso-endo-2-methylaminomethylbicyclo[2.2.2]oct-5-ene cyclize at the C-6 position, since the relevant reacting centers can achieve excellent orbital overlap with minimum molecular motion in comparison to the alternative cyclization path at the C-5 position. The photolysis of the former compound gave a C-nitroso compound which underwent a series of unusual intramolecular cleavages, deoximations, and redox reactions during the work-up. Stereoelectronic requirements for these intramolecular reactions are discussed. Thermolysis of N-chloro-endo-2-methylaminomethylbicyclo[2.2.2]oct-5-en in methanol also gave the product with azaisotwistane skeleton.
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