Yunqing Zhao , Huiyun Ma , Yanxue Bi , Jianghao Ren , Chenting Yan , Gaofeng Bian , Zhifang Li
{"title":"由相应的锡炔和磷酸乙酯钠形成可逆的类锡炔","authors":"Yunqing Zhao , Huiyun Ma , Yanxue Bi , Jianghao Ren , Chenting Yan , Gaofeng Bian , Zhifang Li","doi":"10.1002/ejoc.202500002","DOIUrl":null,"url":null,"abstract":"<div><div>This study reports the synthesis of a novel stannylenoid <strong>2</strong> through the reaction of dialkylstannylene with sodium phosphaethynolate (NaOCP), followed by investigation of its reactivity and stability. Stannylenoid <strong>2</strong> exhibits high stability in THF and remains intact under elevated temperatures for extended periods. Upon irradiation, <strong>2</strong> undergoes CO release reaction, forming a highly stable compound <strong>7</strong>. The solid‐state structure of <strong>7</strong>, 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.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202500002"},"PeriodicalIF":2.5000,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate\",\"authors\":\"Yunqing Zhao , Huiyun Ma , Yanxue Bi , Jianghao Ren , Chenting Yan , Gaofeng Bian , Zhifang Li\",\"doi\":\"10.1002/ejoc.202500002\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>This study reports the synthesis of a novel stannylenoid <strong>2</strong> through the reaction of dialkylstannylene with sodium phosphaethynolate (NaOCP), followed by investigation of its reactivity and stability. Stannylenoid <strong>2</strong> exhibits high stability in THF and remains intact under elevated temperatures for extended periods. Upon irradiation, <strong>2</strong> undergoes CO release reaction, forming a highly stable compound <strong>7</strong>. The solid‐state structure of <strong>7</strong>, 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.</div></div>\",\"PeriodicalId\":167,\"journal\":{\"name\":\"European Journal of Organic Chemistry\",\"volume\":\"28 16\",\"pages\":\"Article e202500002\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2025-04-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1434193X25001884\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25001884","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate
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.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.