Florian Rigoulet , Albert Artigas , Nawal Ferdi , Michel Giorgi , Yoann Coquerel
{"title":"高价碘氧化三碳[5]螺旋烯","authors":"Florian Rigoulet , Albert Artigas , Nawal Ferdi , Michel Giorgi , Yoann Coquerel","doi":"10.1039/d3qo01439h","DOIUrl":null,"url":null,"abstract":"<div><div>The reactivities of both diastereomers of hexabenzotriphenylene (HBTP), a triple carbo[5]helicene of the formula C<sub>42</sub>H<sub>24</sub>, were examined in the presence of phenyliodine diacetate (PIDA) as an oxidizing agent. The <em>D</em><sub>3</sub>-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the <em>C</em><sub>2</sub>-symmetric diastereomer afforded predominantly a cyclodehydrogenation product. Altogether, this shows that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 23","pages":"Pages 5902-5907"},"PeriodicalIF":0.0000,"publicationDate":"2023-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Oxidation of a triple carbo[5]helicene with hypervalent iodine†\",\"authors\":\"Florian Rigoulet , Albert Artigas , Nawal Ferdi , Michel Giorgi , Yoann Coquerel\",\"doi\":\"10.1039/d3qo01439h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The reactivities of both diastereomers of hexabenzotriphenylene (HBTP), a triple carbo[5]helicene of the formula C<sub>42</sub>H<sub>24</sub>, were examined in the presence of phenyliodine diacetate (PIDA) as an oxidizing agent. The <em>D</em><sub>3</sub>-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the <em>C</em><sub>2</sub>-symmetric diastereomer afforded predominantly a cyclodehydrogenation product. Altogether, this shows that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 23\",\"pages\":\"Pages 5902-5907\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-11-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S205241292300116X\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2023/10/12 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S205241292300116X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/10/12 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Oxidation of a triple carbo[5]helicene with hypervalent iodine†
The reactivities of both diastereomers of hexabenzotriphenylene (HBTP), a triple carbo[5]helicene of the formula C42H24, were examined in the presence of phenyliodine diacetate (PIDA) as an oxidizing agent. The D3-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the C2-symmetric diastereomer afforded predominantly a cyclodehydrogenation product. Altogether, this shows that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.
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