{"title":"Synthesis of Stable Hypervalent Bromine(III) Complexes by in Situ Oxidation with Lewis Acids Containing sp-Hybridized Nitrogen","authors":"Tomohiro Fujino, Tadashi Hyodo, Yuko Otani, Kentaro Yamaguchi, Tomohiko Ohwada","doi":"10.1021/acs.orglett.4c03881","DOIUrl":null,"url":null,"abstract":"Stable hypervalent bromine(III) compounds were synthesized via aryl bromine oxidation with <i>sp</i>-hybridized nitrogen cations generated by oxime N–O bond cleavage in trifluoroacetic acid. The resulting intramolecular N–Br hypervalent bond is effectively stabilized by the planar xanthone structure. The structures and physicochemical properties of these λ<sup>3</sup>-bromanes were characterized by X-ray crystallography, cyclic voltammetry, UV-vis spectroscopy, and computational analysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03881","RegionNum":1,"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
Stable hypervalent bromine(III) compounds were synthesized via aryl bromine oxidation with sp-hybridized nitrogen cations generated by oxime N–O bond cleavage in trifluoroacetic acid. The resulting intramolecular N–Br hypervalent bond is effectively stabilized by the planar xanthone structure. The structures and physicochemical properties of these λ3-bromanes were characterized by X-ray crystallography, cyclic voltammetry, UV-vis spectroscopy, and computational analysis.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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