Investigations on Diazo Compounds and Azides, LV1)
7-(Diazomethyl)cycloheptatrienes by Elertrophilic Diazoalkane SubstitutionThe silver-(diazomethy1)phosphoryl compounds 2a -c smoothly undergo electrophilic diazoalkane substitution with 1 to give 3a-c. In contrast, a more complex product formation is encountered in the reaction of 1 with the mercury-bis(diazomethylcarbony1) compounds 4a -d: Besides the 7-(diazomethyl)cycloheptatrienes 5 a -d the styrene derivatives 6a -c as well as the bromomercurio compounds 'la -d are formed. Probably the norcaradiene intermediates 12 and 14 play a role in the formation of 6 and 7. The reaction of the 7-(diazomethy1)cycloheptatrienes
Die arylsubstituierten Diazoverbindungen l a -h reagieren mit den Triazoldionen 2a-c bei 20°C in Benzol unter Stickstoffverlust zu den stabilen Azomethinimin-Dipolen 4a -p. Ihr 1,3-dipolarer Charakter kommt sowohl in der Addition von Methanol und Ethanol (4d -f + 5 a -f) als auch in Cycloadditionsreaktionen mit Acetylendicarbonsiiure-dimethylester (4d,e + 6a, b) und Phenylisocyanat (4d + 7) zum Ausdruck. Bisdipole erhalt man auf zwei verschiedenen Wegen: Entweder setzt man Bisdiazoverbindungen mit 4-Phenyl-3H-I ,2,4-triazol
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