Abstract
AbstractThe as yet unknown route to triaziridines by the addition of nitrenes to the π side of the NN bond is achieved intramolecularly by the photolysis (thermolysis) of syn‐azo azide substrates with high proximity; the yields reflect the sterical (and possibly inductive) influences of the skeleton. The product composition is rather independent of the exciting light; intramolecular azo → azide energy transfer is assumed. The kinetic skeleton stabilization of the triaziridines permits the synthesis of 17 (18) by the thermolysis of 7 (8) at 200°C with the product composition deviating only marginally from that of the photolysis. Attempts towards enlargement of the triaziridines to N3X rings (XCHR, O, NR) lead exclusively to products of intramolecular fragmentation.
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