Reactions of β-sultones and carbyl sulfates with nucleophiles

✍ Scribed by Bert H. Bakker; Ruud M. Schonk; Hans Cerfontain

• Book ID: 104589407
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 457 KB
• Volume: 111
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19921110405

✦ Synopsis

Abstract

Ring opening of the octane‐β‐sultones 1a‐c by methanol gives the β‐methoxyoctane‐sulfonic acids 2a‐c by S~N~2 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], respectively, by a similar S~N~2 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.