{"title":"Bromomethyl ß-styryl and ß-bromostyryl sulfones in the Michael-induced Ramberg-Bäcklund reaction","authors":"V. Vasin, I. Bolusheva, V. Razin","doi":"10.1080/0278611031000107111","DOIUrl":null,"url":null,"abstract":"The UV-initiated addition of bromomethane sulfonyl bromide to phenylacetylene (quartz test tube, CH2Cl2, 20 °C) gives bromomethyl (E)-2-bromo-2-phenylethenyl sulfone. In a similar reaction with styrene, bromomethyl 2-bromo-2-phenylethyl sulfone is formed. Subsequent dehydrobromination of this adduct (Na2CO3 in aqueous dioxane, 20 °C) gives bromomethyl (E)-2-phenylethenyl sulfone, which is transformed by bromination-dehydrobromination (Br2 in CCl4 at 20 °C, then Na2CO3 in aqueous dioxane, 50 °C) into bromomethyl (Z)-1-bromo-2-phenylethenyl sulfone. Upon heating in methanol in the presence of sodium methoxide, the unsaturated sulfones enter the Michael-induced Ramberg-Bäcklund reaction. Monobromo-substituted derivative transforms into 1-(1-methoxy-2-propenyl)benzene. Dibromosubstituted derivatives give 1-(1,1-dimethoxy-2-propenyl)benzene via intermediate formation of bromomethyl 2-methoxy-2-phenylethenyl sulfone through elimination-addition or vinylic substitution.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"9","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Sulfur Letters","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1080/0278611031000107111","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 9
Abstract
The UV-initiated addition of bromomethane sulfonyl bromide to phenylacetylene (quartz test tube, CH2Cl2, 20 °C) gives bromomethyl (E)-2-bromo-2-phenylethenyl sulfone. In a similar reaction with styrene, bromomethyl 2-bromo-2-phenylethyl sulfone is formed. Subsequent dehydrobromination of this adduct (Na2CO3 in aqueous dioxane, 20 °C) gives bromomethyl (E)-2-phenylethenyl sulfone, which is transformed by bromination-dehydrobromination (Br2 in CCl4 at 20 °C, then Na2CO3 in aqueous dioxane, 50 °C) into bromomethyl (Z)-1-bromo-2-phenylethenyl sulfone. Upon heating in methanol in the presence of sodium methoxide, the unsaturated sulfones enter the Michael-induced Ramberg-Bäcklund reaction. Monobromo-substituted derivative transforms into 1-(1-methoxy-2-propenyl)benzene. Dibromosubstituted derivatives give 1-(1,1-dimethoxy-2-propenyl)benzene via intermediate formation of bromomethyl 2-methoxy-2-phenylethenyl sulfone through elimination-addition or vinylic substitution.