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Phospholenes from Phosphabenzenes by Selective Ring Contraction

Lin, Jinxiong; Coles, Nathan T.; Dettling, Lea; Steiner, Luca; Witte, Jan Felix; Paulus, Beate; Müller, Christian

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Authors

Jinxiong Lin

Lea Dettling

Luca Steiner

Jan Felix Witte

Beate Paulus

Christian Müller



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.

Citation

Lin, J., Coles, N. T., Dettling, L., Steiner, L., Witte, J. F., Paulus, B., & Müller, C. (2022). Phospholenes from Phosphabenzenes by Selective Ring Contraction. Chemistry - A European Journal, 28(72), Article e202203406. https://doi.org/10.1002/chem.202203406

Journal Article Type Article
Acceptance Date Nov 16, 2022
Online Publication Date Nov 16, 2022
Publication Date Dec 27, 2022
Deposit Date Dec 20, 2022
Publicly Available Date Dec 20, 2022
Journal Chemistry – A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Peer Reviewed Peer Reviewed
Volume 28
Issue 72
Article Number e202203406
DOI https://doi.org/10.1002/chem.202203406
Keywords General Chemistry, Catalysis, Organic Chemistry
Public URL https://nottingham-repository.worktribe.com/output/14304688
Publisher URL https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202203406

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