Bromomethyl ß-styryl and ß-bromostyryl sulfones in the Michael-induced Ramberg-Bäcklund reaction

V. Vasin, I. Bolusheva, V. Razin
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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.
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michael诱导Ramberg-Bäcklund反应中的溴乙基ß-苯乙烯基和ß-溴苯乙烯基砜
紫外引发溴甲烷磺酰溴与苯乙炔(石英试管,CH2Cl2, 20°C)加成得到溴乙基(E)-2-溴-2-苯乙烯基砜。在与苯乙烯的类似反应中,生成2-溴-2-溴-苯乙基砜。随后,该加合物(Na2CO3在二氧六环中,20℃)脱氢溴化得到溴甲基(E)-2-苯乙烯基砜,溴化-脱氢溴化(Br2在CCl4中,20℃,Na2CO3在二氧六环中,50℃)转化为溴甲基(Z)-1-溴-2-苯乙烯基砜。在甲醇存在下加热时,不饱和砜进入迈克尔诱导的Ramberg-Bäcklund反应。单溴取代衍生物转化为1-(1-甲氧基-2-丙烯基)苯。二溴取代衍生物通过消除加成或乙烯基取代中间体生成2-甲氧基-2-苯乙烯基砜,得到1-(1,1-二甲氧基-2-丙烯基)苯。
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