Rui Wei, Fengbo Huang, Xiaofang Lan, Qiuming Liang, Liu Leo Liu
{"title":"点击化学:重氮甲基阴离子与不饱和键的反应†","authors":"Rui Wei, Fengbo Huang, Xiaofang Lan, Qiuming Liang, Liu Leo Liu","doi":"10.1002/cjoc.70026","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>The reactions of potassium diazaphospholidinyl diazomethylide with phenylacetylene, acetonitrile, adamantyl phosphaalkyne, and styrene promptly form pyrazolide, triazolide, diazaphospholide, and pyrazolinide, respectively. The reaction mechanisms have been studied using DFT calculations. While the reactions with phenylacetylene and styrene proceed via stepwise pathways, those with acetonitrile and adamantyl phosphaalkyne follow concerted pathways. Additionally, the pyrazolide product readily undergoes <i>N</i>-functionalization, yielding methyl pyrazole, germanyl pyrazole, and copper pyrazolide complexes.</p>\n <p></p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 13","pages":"1547-1552"},"PeriodicalIF":5.5000,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Click Chemistry: Reactions of a Diazomethyl Anion with Unsaturated Bonds†\",\"authors\":\"Rui Wei, Fengbo Huang, Xiaofang Lan, Qiuming Liang, Liu Leo Liu\",\"doi\":\"10.1002/cjoc.70026\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>The reactions of potassium diazaphospholidinyl diazomethylide with phenylacetylene, acetonitrile, adamantyl phosphaalkyne, and styrene promptly form pyrazolide, triazolide, diazaphospholide, and pyrazolinide, respectively. The reaction mechanisms have been studied using DFT calculations. While the reactions with phenylacetylene and styrene proceed via stepwise pathways, those with acetonitrile and adamantyl phosphaalkyne follow concerted pathways. Additionally, the pyrazolide product readily undergoes <i>N</i>-functionalization, yielding methyl pyrazole, germanyl pyrazole, and copper pyrazolide complexes.</p>\\n <p></p>\\n </div>\",\"PeriodicalId\":151,\"journal\":{\"name\":\"Chinese Journal of Chemistry\",\"volume\":\"43 13\",\"pages\":\"1547-1552\"},\"PeriodicalIF\":5.5000,\"publicationDate\":\"2025-04-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70026\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70026","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Click Chemistry: Reactions of a Diazomethyl Anion with Unsaturated Bonds†
The reactions of potassium diazaphospholidinyl diazomethylide with phenylacetylene, acetonitrile, adamantyl phosphaalkyne, and styrene promptly form pyrazolide, triazolide, diazaphospholide, and pyrazolinide, respectively. The reaction mechanisms have been studied using DFT calculations. While the reactions with phenylacetylene and styrene proceed via stepwise pathways, those with acetonitrile and adamantyl phosphaalkyne follow concerted pathways. Additionally, the pyrazolide product readily undergoes N-functionalization, yielding methyl pyrazole, germanyl pyrazole, and copper pyrazolide complexes.
期刊介绍:
The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.