环双联苯羰基的Wittig反应。

IF 2.1 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-07-14 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.107

Taito Moribe, Junichiro Hirano, Hideaki Takano, Hiroshi Shinokubo, Norihito Fukui

{"title":"环双联苯羰基的Wittig反应。","authors":"Taito Moribe, Junichiro Hirano, Hideaki Takano, Hiroshi Shinokubo, Norihito Fukui","doi":"10.3762/bjoc.21.107","DOIUrl":null,"url":null,"abstract":"Cyclobisbiphenylenecarbonyl (CBBC) represents a readily available chiral figure-eight macrocycle containing two carbonyl groups. However, the transformation of the carbonyl groups has been unexplored. Herein, we conducted the Wittig reaction of CBBC with methylenetriphenylphosphorane to furnish two chiral macrocycles containing one or two exocyclic olefin units. Owing to the transformation of carbonyl groups, the resulting products exhibit several unique physical and chemical properties: (1) the enhancement of configurational stability, (2) the appearance of fluorescence, and (3) the reductive carbon-carbon-bond formation between carbonyl and alkene units.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1454-1461"},"PeriodicalIF":2.1000,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12278106/pdf/","citationCount":"0","resultStr":"{\"title\":\"Wittig reaction of cyclobisbiphenylenecarbonyl.\",\"authors\":\"Taito Moribe, Junichiro Hirano, Hideaki Takano, Hiroshi Shinokubo, Norihito Fukui\",\"doi\":\"10.3762/bjoc.21.107\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Cyclobisbiphenylenecarbonyl (CBBC) represents a readily available chiral figure-eight macrocycle containing two carbonyl groups. However, the transformation of the carbonyl groups has been unexplored. Herein, we conducted the Wittig reaction of CBBC with methylenetriphenylphosphorane to furnish two chiral macrocycles containing one or two exocyclic olefin units. Owing to the transformation of carbonyl groups, the resulting products exhibit several unique physical and chemical properties: (1) the enhancement of configurational stability, (2) the appearance of fluorescence, and (3) the reductive carbon-carbon-bond formation between carbonyl and alkene units.\",\"PeriodicalId\":8756,\"journal\":{\"name\":\"Beilstein Journal of Organic Chemistry\",\"volume\":\"21 \",\"pages\":\"1454-1461\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2025-07-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12278106/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Beilstein Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3762/bjoc.21.107\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.21.107","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

环双联苯羰基（CBBC）是一种含有两个羰基的易于获得的手性8型大环。然而，羰基的转化尚未被探索。在此，我们将CBBC与亚甲基三苯基磷烷进行了Wittig反应，得到了两个含有一个或两个外环烯烃单元的手性大环。由于羰基的转变，所得到的产物表现出几种独特的物理和化学性质：(1)增强了构型稳定性，(2)荧光的出现，(3)羰基和烯烃单元之间形成了还原性的碳-碳键。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Wittig reaction of cyclobisbiphenylenecarbonyl.

Cyclobisbiphenylenecarbonyl (CBBC) represents a readily available chiral figure-eight macrocycle containing two carbonyl groups. However, the transformation of the carbonyl groups has been unexplored. Herein, we conducted the Wittig reaction of CBBC with methylenetriphenylphosphorane to furnish two chiral macrocycles containing one or two exocyclic olefin units. Owing to the transformation of carbonyl groups, the resulting products exhibit several unique physical and chemical properties: (1) the enhancement of configurational stability, (2) the appearance of fluorescence, and (3) the reductive carbon-carbon-bond formation between carbonyl and alkene units.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.