Gradl S, Köckenberger J, Oppl J, Schiller M, Heinrich M (2021)
Publication Type: Journal article
Publication year: 2021
The synthesis of pyridazinium salts was achieved from readily available phenylazosulfonates in a single reaction step. The reaction proceeds via the formation of short-lived phenyldiazenes, which-owing to the strongly acidic conditions-are partially protonated. The phenyldiazenes then undergo a rapid cycloaddition to furans to give pyridazinium salts via elimination of water. The fact that the pyridazinium synthesis shows a low sensitivity toward oxygen, although phenyldiazenes occur as intermediates, can be explained by the very fast cycloaddition step and the partial protonation of the phenyldiazene.
APA:
Gradl, S., Köckenberger, J., Oppl, J., Schiller, M., & Heinrich, M. (2021). Synthetic Route to Phenyl Diazenes and Pyridazinium Salts from Phenylazosulfonates. Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.1c00013
MLA:
Gradl, Susanne, et al. "Synthetic Route to Phenyl Diazenes and Pyridazinium Salts from Phenylazosulfonates." Journal of Organic Chemistry (2021).
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