{"title":"Ketocalixarenes: Versatile yet still Unexplored Macrocycles","authors":"Ori Shalev, Silvio E. Biali","doi":"10.1055/s-0043-1775380","DOIUrl":null,"url":null,"abstract":"<p>Ketocalix[<i>n</i>]arenes can be prepared via oxidation of the methylene groups of protected calix[<i>n</i>]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[<i>n</i>]radialenes.</p> <p>1\tIntroduction</p> <p>2 Synthesis of Ketocalix[<i>n</i>]arenes</p> <p>2.1 Ketocalix[4]arene Derivatives</p> <p>2.2 Systems Possessing both Carbonyl and Bromomethane Bridges</p> <p>2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives</p> <p>2.4 Monooxo- and Dioxoketocalix[6]arenes</p> <p>3 Conformation of Ketocalixarenes</p> <p>4 Reactions of Ketocalixarenes</p> <p>4.1 Alkylation of the OH Groups</p> <p>4.2 Intramolecular Aromatic Nucleophilic Substitution</p> <p>4.3 Reduction of the Carbonyl Groups</p> <p>4.4 Reaction of <b>5c</b> with PhLi</p> <p>4.5 Reaction with <i>tert</i>-Butyllithium</p> <p>5 From Ketocalix[<i>n</i>]arenes to Calix[<i>n</i>]radialenes and Calix[<i>n</i>]rotanes</p> <p>6 Summary and Outlook</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/s-0043-1775380","RegionNum":4,"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
Ketocalix[n]arenes can be prepared via oxidation of the methylene groups of protected calix[n]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[n]radialenes.
1 Introduction
2 Synthesis of Ketocalix[n]arenes
2.1 Ketocalix[4]arene Derivatives
2.2 Systems Possessing both Carbonyl and Bromomethane Bridges
2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives
期刊介绍:
SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.