Abstract
The reactions of erythro- and threo-1-chloro- and -1-bromo-1,2-diphenyl-2-p-tolylsulphonyiethanes (IH)–(IVH) and of the 1,2-dideuterio-derivatives (ID)–(IVD) with methoxide ion in methanol and with triethylamine in benzene have been followed kinetically. For methoxide ion the reactions of the erythro-isomers (anti-elimination) are much faster than those of the threo-derivatives (syn+anti-elimination). The sensitivity to the leaving group is rather modest for both isomers whereas reaction rates are markedly influenced by isotopic substitution. In the reactions with amine the kerythro : kthreo ratios become much smaller and kBr : kCl values close to unity are observed for the latter isomer. Isotope effects are higher for syn- than for anti-elimination. These and related observations are evaluated in terms of an E2 mechanism involving a small degree of C–X breakage in the transition state or an E1cB mechanism of irreversible type.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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