Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

The Synthesis of Trans-enediones From Furan Derivatives Using Pyridinium Chlorochromate. An Explanation

Version 1 : Received: 7 October 2023 / Approved: 9 October 2023 / Online: 10 October 2023 (03:01:11 CEST)

How to cite: D’Auria, M.; Langerame, F. The Synthesis of Trans-enediones From Furan Derivatives Using Pyridinium Chlorochromate. An Explanation. Preprints 2023, 2023100516. https://doi.org/10.20944/preprints202310.0516.v1 D’Auria, M.; Langerame, F. The Synthesis of Trans-enediones From Furan Derivatives Using Pyridinium Chlorochromate. An Explanation. Preprints 2023, 2023100516. https://doi.org/10.20944/preprints202310.0516.v1

Abstract

The reaction of pyridinium chlorochromate with furan to give enedione derivatives cannot be performed by using commercial PCC. Homemade and commercial PCC had different color and showed some differences in the XRD spectrum. XPS showed the presence of relevant amount of Cr(III) in the homemade reagent. DFT calculations showed that Cr(III) impurities in the reagent can catalyze the reaction with furan derivatives, if oxygen atom in the Cr(III) derivative attacks the furan ring, while it is reoxidized by PCC, through a migration of a chlorine atom.

Keywords

Pyridinium chlorochromate; furan oxidation; enediones synthesis; XRD; XPS; DFT calculations

Subject

Chemistry and Materials Science, Organic Chemistry

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