Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent

✍ Scribed by Pablo J Linares-Palomino; Sofı́a Salido; Joaquı́n Altarejos; Adolfo Sánchez

• Book ID: 104254233
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 195 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01635-6

✦ Synopsis

Among several sulfonic acids studied (MeSO 3 H, p-TsOH, H 2 SO 4 , ClSO 3 H, FSO 3 H), the scarcely used chlorosulfonic acid showed to be an efficient agent for electrophilic olefin cyclizations with internal nucleophilic termination, in a similar manner that is well-established with fluorosulfonic acid. Its availability, lower price and relatively lesser handling problems makes ClSO 3 H an advantageous cyclizing agent particularly for high-scale applications. The stereochemical outcome of these cyclizations has been rationalized.