Publication: Unveiling the Phosphine-Mediated N‑Transfer from Azide to Isocyanide en Route to Carbodiimides and 4‑Imino-1,3,2-diazaphosphetidines
Authors
Pastor, Aurelia ; Lopez-Leonardo, Carmen ; Cutillas-Font, Guillermo ; Martinez-Cuezva, Alberto ; Marin-Luna, Marta ; Garcia-Lopez, Jose-Antonio ; Saura-Llamas, Isabel ; Alajarín, Mateo
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Publisher
American Chemical Society
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DOI
https://doi.org/10.1021/acs.orglett.4c03902
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info:eu-repo/semantics/article
Description
© 2025 American Chemical Society.____
This document is the published version of a published work that appeared in final This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by/4.0 ____
To access the final edited and published work see:
https://doi.org/10.1021acs.orglett.4c03902
Abstract
Intramolecular reactions between isocyano and iminophosphorane functions yield species containing an embedded 1,3,2-diazaphosphetidine ring, as result of the [2 + 2] cycloaddition of the primary reactive product, the cyclic carbodiimide, with a second unit of reactant. DFT studies reveal a first rate-determining step entailing a [2 +1] cycloaddition involving the isocyanide carbon atom and the P N double bond, with the further intervention of a dipolar precursor of the intermediate carbodiimide. The 1,3,2-diazaphosphetidine ring of the final products is shown to be hydrolytically and thermally labile.
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Citation
Organic Letters, 27, 2025, 73-79
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