Tetrahedron

Mechanisms of elimination reactions—XXVII: The reactions of 1-arylethyldimethylsulfonium bromides with sodium ethoxide in ethanol

FL Roe, WH Saunders

文献索引：Roe,F.L.; Saunders,W.H. Tetrahedron, 1977 , vol. 33, p. 1581 - 1585

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被引用次数: 7

摘要

Treatment of 1-phenylethyldimethylsulfonium bromide 1 with sodium ethoxide in ethanol at 35° affords four products by five reaction paths: styrene 2 by E2 and α'-β mechanisms, ethyl 1-phenylethyl ether 3 and methyl 1-phenylethyl sulfide 4 by the SN2 mechanism, and methyl o-ethylbenzyl sulfide 5 by a Sommelet-Hauser rearrangement. Isotope effects of 5.9 and 3.5 for E2 and α'-β reactions were estimated by comparing the deuterium content of methyl ...