{"title":"Non-electronic activation of aromatic frameworks by steric repulsion between peri-substituents","authors":"Annisa Indah Reza and Nagatoshi Nishiwaki","doi":"10.1039/D5OB00118H","DOIUrl":null,"url":null,"abstract":"<p >Distortion of coplanarity has been known as one of the activation methods for planar aromatic rings, and a great deal of effort has been devoted to experimental and computational studies. However, there is no study on systematic evaluation for distortion by steric repulsion between substituents. Inspired by this fact, several studies have focused on non-electronic activation caused by steric interactions between <em>peri</em>-substituents. These studies indicated systematically and quantitatively how varying the bulkiness of substituents affects the distortion and the resulting dearomatization, and changes in reactivity due to the distortion (<em>e.g.</em>, non-electronic activation) were also compared. Furthermore, this concept is applied to 1,8-dihalonaphthalenes to afford unsymmetrical products <em>via</em> the halogen dance reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 15","pages":" 3483-3491"},"PeriodicalIF":2.9000,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00118h","RegionNum":3,"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
Distortion of coplanarity has been known as one of the activation methods for planar aromatic rings, and a great deal of effort has been devoted to experimental and computational studies. However, there is no study on systematic evaluation for distortion by steric repulsion between substituents. Inspired by this fact, several studies have focused on non-electronic activation caused by steric interactions between peri-substituents. These studies indicated systematically and quantitatively how varying the bulkiness of substituents affects the distortion and the resulting dearomatization, and changes in reactivity due to the distortion (e.g., non-electronic activation) were also compared. Furthermore, this concept is applied to 1,8-dihalonaphthalenes to afford unsymmetrical products via the halogen dance reaction.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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