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

Journal of Organic Chemistry American Chemical Society

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.

Authors with CRIS profile

Susanne Gradl Professur für Pharmazeutische Chemie Johannes Köckenberger Lehrstuhl für Pharmazeutische Chemie Markus Heinrich Professur für Pharmazeutische Chemie

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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