Nucleophilic displacement by hydrogen carbonate anion, and its implications in the oxidation of alkyl toluene-p-sulphonates with dimethyl sulphoxide–sodium hydrogen carbonate

Abstract

Hydrogen carbonate anion is shown to be a more effective nucleophile than dimethyl sulphoxide in reactions with c-3-hydroxy-2-methyl-4-p-tolylnorbornan-r-2-ylmethyl toluene-p-sulphonate (I) and with 3-hydroxy-2,2-dimethyl-3-phenylpropyl toluene-p-sulphonate (IX; R = Ts). The elements of carbon dioxide are retained in the product as a cyclic carbonate system.