{"title":"GeCl2-Mediated Ring Contraction toward Endofullerenes","authors":"Shumpei Sadai, Yoshifumi Hashikawa, Yasujiro Murata","doi":"10.1021/acs.joc.5c00217","DOIUrl":null,"url":null,"abstract":"Germanium(II) dichloride dioxane complex (GeCl<sub>2</sub>·dioxane) is often utilized as a source of molecular germylene, i.e., GeCl<sub>2</sub>, which is known to undergo oxidative 1,4-addition to conjugated substrates. Inspired by this nature resembled to carbenes, we demonstrated a C═C bond formation from two carbonyl moieties engaged in an aromatic macrocycle. This germylene-mediated reaction enables us to realize efficient synthesis of endo[60]fullerenes through the consecutive ring contraction of open-[60]fullerenes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00217","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Germanium(II) dichloride dioxane complex (GeCl2·dioxane) is often utilized as a source of molecular germylene, i.e., GeCl2, which is known to undergo oxidative 1,4-addition to conjugated substrates. Inspired by this nature resembled to carbenes, we demonstrated a C═C bond formation from two carbonyl moieties engaged in an aromatic macrocycle. This germylene-mediated reaction enables us to realize efficient synthesis of endo[60]fullerenes through the consecutive ring contraction of open-[60]fullerenes.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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