Ban Kinoshita, Saki Maejima, Yuta Niki, K. Mitsudo, Seiji Suga, Hideki Yorimitsu
{"title":"[1,2]-Retro-Brook Rearrangement Induced by Electrochemical Reduction of Silyl Enolates","authors":"Ban Kinoshita, Saki Maejima, Yuta Niki, K. Mitsudo, Seiji Suga, Hideki Yorimitsu","doi":"10.1093/bulcsj/uoae038","DOIUrl":null,"url":null,"abstract":"\n Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulletin of the Chemical Society of Japan","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1093/bulcsj/uoae038","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.
期刊介绍：
The Bulletin of the Chemical Society of Japan (BCSJ) is devoted to the publication of scientific research papers in the fields of Theoretical and Physical Chemistry, Analytical and Inorganic Chemistry, Organic and Biological Chemistry, and Applied and Materials Chemistry. BCSJ appears as a monthly journal online and in advance with three kinds of papers (Accounts, Articles, and Short Articles) describing original research. The purpose of BCSJ is to select and publish the most important papers with the broadest significance to the chemistry community in general. The Chemical Society of Japan hopes all visitors will notice the usefulness of our journal and the abundance of topics, and welcomes more submissions from scientists all over the world.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
