Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate

Abstract This study reports the synthesis of a novel stannylenoid 2 through the reaction of dialkylstannylene with sodium phosphaethynolate (NaOCP), followed by investigation of its reactivity and stability. Stannylenoid 2 exhibits high stability in THF and remains intact under elevated temperatures for extended periods. Upon irradiation, 2 undergoes CO release reaction, forming a highly stable compound 7 . The solid‐state structure of 7 , determined by single‐crystal X‐ray diffraction, reveals a diamond‐shaped Sn₂P₂ moiety with distorted tetrahedral geometry. Computational studies using density functional theory (DFT) confirm the experimental findings, showing strong Sn−P bonding and a nucleophilic character for the phosphorus atoms. The results provide new insights into the reactivity of stannylenoids and their potential applications in synthetic chemistry.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-03-19
DOI
https://doi.org/10.1002/ejoc.202500002
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate

Hongwei Ma, Jianghao Ren, Chenting Yan, Y. BI et al.
European Journal of Organic Chemistry
Organophosphorus compounds synthesis
article

Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate

Hongwei Ma, Jianghao Ren, Chenting Yan, Y. BI, Zhifang Li, Yunqing Zhao, Gaofeng Bian
article en

Abstract

Abstract This study reports the synthesis of a novel stannylenoid 2 through the reaction of dialkylstannylene with sodium phosphaethynolate (NaOCP), followed by investigation of its reactivity and stability. Stannylenoid 2 exhibits high stability in THF and remains intact under elevated temperatures for extended periods. Upon irradiation, 2 undergoes CO release reaction, forming a highly stable compound 7 . The solid‐state structure of 7 , determined by single‐crystal X‐ray diffraction, reveals a diamond‐shaped Sn₂P₂ moiety with distorted tetrahedral geometry. Computational studies using density functional theory (DFT) confirm the experimental findings, showing strong Sn−P bonding and a nucleophilic character for the phosphorus atoms. The results provide new insights into the reactivity of stannylenoids and their potential applications in synthetic chemistry.

European Journal of Organic ChemistryVol. 28(16)
Hangzhou Normal University (CN)
Openalex Percentile: Top 96%
Organophosphorus compounds synthesis
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Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate — Hongwei Ma, Jianghao Ren, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS