Phospholenes from phosphabenzenes by selective ring contraction

Lin, Jinxiong, Coles, Nathan T. ORCID: https://orcid.org/0000-0001-6190-9080, Dettling, Lea, Steiner, Luca, Witte, J. Felix, Paulus, Beate and Müller, Christian 2022. Phospholenes from phosphabenzenes by selective ring contraction. Chemistry - A European Journal 28 (72) , e202203406. 10.1002/chem.202203406

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Abstract

A 3-amino-functionalized phosphabenzene (phosphinine) has been synthesized and structurally characterized. The pyramidalized nitrogen atom of the dimethylamino substituent indicates only a weak interaction between the lone pair of the nitrogen atom and the aromatic phosphorus heterocycle, resulting in somewhat basic character. It turned out that the amino group can indeed be protonated by HCl. In contrast to pyridines, however, the phosphabenzene-ammonium salt undergoes a selective ring contraction to form a hydroxylphospholene oxide in the presence of additional water. Based on deuterium labeling experiments and quantum chemical calculations, a rational mechanism for this hitherto unknown conversion is proposed.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	0947-6539
Date of First Compliant Deposit:	4 December 2024
Date of Acceptance:	16 November 2022
Last Modified:	06 Jan 2025 10:03
URI:	https://orca.cardiff.ac.uk/id/eprint/173584

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