Mechanisms of elimination reactions—XXVII

摘要: Abstract Treatment of 1-phenylethyldimethylsulfonium bromide 1 with sodium ethoxide in ethanol at 35° affords four products by five reaction paths: styrene 2 E2 and α'-β mechanisms, ethyl 1-phenylethyl ether 3 methyl sulfide 4 the S N mechanism, o -ethylbenzyl 5 a Sommelet-Hauser rearrangement. Isotope effects 5.9 3.5 for reactions were estimated comparing deuterium content from β-d , α-d 7 (all α-positions exchanged) sulfonium salt. Product analyses on unsubstituted, p -methyl, -fluoro, -bromo m -chloro salts combined overall rates to calculate partial formation each product. These fitted Hammett equation give values product as follows: 0.95±0.19; −0.63±0.41; 0.95±0.11; 4.84±0.38. The mechanistic implications results are discussed.