Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent

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• 作者：Linares-Palomino ; Pablo J. ; Salido ; Sofí ; a ; Altarejos ; Joaquí ; n ; Sá ; nchez ; Adolfo
• 关键词：chlorosulfonic acid ; sulfonic acids ; electrophilic olefin cyclization ; benzopyrans ; odorants
• 刊名：Tetrahedron Letters
• 出版年：2003
• 出版时间：August 25, 2003
• 年：2003
• 卷：44
• 期：35
• 页码：6651-6655
• 全文大小：195 K

文摘

Among several sulfonic acids studied (MeSO₃H, p-TsOH, H₂SO₄, ClSO₃H, FSO₃H), 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 ClSO₃H an advantageous cyclizing agent particularly for high-scale applications. The stereochemical outcome of these cyclizations has been rationalized.