Reactions of β??sultones and carbyl sulfates with nucleophiles

…, RM Schonk, H Cerfontain

Index: Schonk, Ruud M.; Bakker, Bert H.; Cerfontain, Hans Recueil des Travaux Chimiques des Pays-Bas, 1992 , vol. 111, # 1 p. 49 - 55

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Citation Number: 3

Abstract

Abstract Ring opening of the octane-β-sultones 1a-c by methanol gives the β- methoxyoctane-sulfonic acids 2a-c by SN 2 substitution at CO with inversion of the configuration. Hydrolysis of cis-and trans-4, 5-octanesultones 1a-b under acidic conditions is stereospecific and leads to threo-[(RR, SS)-4u] and erythro-5-hydroxy-4-octanesulfonic acid [(RS, SR)-4u], respectively, by a similar SN 2 reaction on the carbon of the C [BOND] O ...