Synthetic Route to Phenyl Diazenes and Pyridazinium Salts from Phenylazosulfonates

Gradl S, Köckenberger J, Oppl J, Schiller M, Heinrich M (2021)


Publication Type: Journal article

Publication year: 2021

Journal

DOI: 10.1021/acs.joc.1c00013

Abstract

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.

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How to cite

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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