{"title":"Study on the development of radical building block: Mn(III)-based reaction of 1,3-indanedione","authors":"Kazuki Hisano , Hiroshi Nishino","doi":"10.1080/00397911.2024.2385542","DOIUrl":null,"url":null,"abstract":"<div><p>The Mn(III)-based oxidation of 1,3-indanedione (<strong>1</strong>) with 1,1-diarylethenes <strong>2a–c</strong> effectively proceeded in boiling AcOH to produce 2,2-bis(vinyl)indanediones <strong>5a–c</strong> and 1,2’-spirobi[indene]-1’,3’-diones <strong>6a–c</strong> via the formation of 2,2-bis(2-acetoxyethyl)indanedione <strong>3</strong> and acetoxyindeno[1,2-b]furan-4-one <strong>4</strong> intermediates. On the other hand, the Mn(III)-based aerobic oxidation of <strong>1a</strong> with <strong>2a</strong> at room temperature resulted in bis(endoperoxide) <strong>8a</strong> and endoperoxypropellane <strong>9a</strong> via the production of mono(endoperoxide) <strong>7a</strong>. The plausible reaction pathways were also discussed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1332-1343"},"PeriodicalIF":1.8000,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000808","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The Mn(III)-based oxidation of 1,3-indanedione (1) with 1,1-diarylethenes 2a–c effectively proceeded in boiling AcOH to produce 2,2-bis(vinyl)indanediones 5a–c and 1,2’-spirobi[indene]-1’,3’-diones 6a–c via the formation of 2,2-bis(2-acetoxyethyl)indanedione 3 and acetoxyindeno[1,2-b]furan-4-one 4 intermediates. On the other hand, the Mn(III)-based aerobic oxidation of 1a with 2a at room temperature resulted in bis(endoperoxide) 8a and endoperoxypropellane 9a via the production of mono(endoperoxide) 7a. The plausible reaction pathways were also discussed.
期刊介绍：
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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