Reactions of β-sultones and carbyl sulfates with nucleophiles

Article abstract of DOI:10.1002/recl.19921110405

Ring opening of the octane-β-sultones 1a-c by methanol gives the β-methoxyoctanesulfonic acids 2a-c by SN2 substitution at C-O 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>, respcectively, by a similar SN2 reaction on the carbon of the C-O bond.Hydrolysis of 4,5-octanesultones 1a-b with base proceeds by attack at the sulfur atom of the β-sultone ring to provide 5-hydroxy-4-octanesulfonates (4v) with retention.Reaction of carbyl sulfates 5a-b with methanol gives the methyl esters of 5-hydroxy-4-octanesulfonic acid 7a-b in a stereospecific way with retention of configuration by attack of methanol at the sulfonate sulfur atom.