{"title":"Reactions of 2,2-dialkyl-1,2-dihydroquinolines. Part VI. Further bromination studies","authors":"J. P. Brown, O. Meth–Cohn","doi":"10.1039/J39710003631","DOIUrl":null,"url":null,"abstract":"The product obtained by tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in methanol described by Cliffe is not identical with 3,6,8-tribromo-4-bromomethyl-1,2-dihydro-2,2-dimethylquinoline, the tetrabromination product obtained in chloroform. It has been identified as the isomeric compound 3,6,8-tribromo-4-bromomethylene-1,2,3,4-tetrahydro-2,2-dimethylquinoline. This reacts with aqueous ethanolic alkali to yield an unusual fused aziridine. Further bromination, or nitration, yields dihydroquinolines, accompanied in the former case by a product of oxidative dimerisation which is also the main product of attempted tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in sulphuric acid.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"55 1","pages":"3631-3634"},"PeriodicalIF":0.0000,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society C: Organic","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/J39710003631","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 3
Abstract
The product obtained by tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in methanol described by Cliffe is not identical with 3,6,8-tribromo-4-bromomethyl-1,2-dihydro-2,2-dimethylquinoline, the tetrabromination product obtained in chloroform. It has been identified as the isomeric compound 3,6,8-tribromo-4-bromomethylene-1,2,3,4-tetrahydro-2,2-dimethylquinoline. This reacts with aqueous ethanolic alkali to yield an unusual fused aziridine. Further bromination, or nitration, yields dihydroquinolines, accompanied in the former case by a product of oxidative dimerisation which is also the main product of attempted tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in sulphuric acid.
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