Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O -silylated cinnamyl alcohols
{"title":"Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O -silylated cinnamyl alcohols","authors":"S. Menichetti, C. Stirling","doi":"10.1039/B109805E","DOIUrl":null,"url":null,"abstract":"A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3.","PeriodicalId":17267,"journal":{"name":"Journal of The Chemical Society-perkin Transactions 1","volume":"3 1","pages":"28-30"},"PeriodicalIF":0.0000,"publicationDate":"2002-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society-perkin Transactions 1","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/B109805E","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 2
Abstract
A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3.