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Unusual cyclization and Sn′-type displacement of carbazole sulfoxide under Pummerer reaction conditions

✍ Scribed by Tomomi Kawasaki; Hirohide Suzuki; Ikuhiro Sakata; Hiroyuki Nakanishi; Masanori Sakamoto

Book ID
104256941
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
119 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Trifluoroacetic anhydride induced Pummerer reactions of carbazole-sulfoxide 1 follow an unusual pathway, in which the initially formed acyloxysulfonium salt 3 undergoes not the usual abstract of m-proton but internal nucleophilic substitution with the indole nuclear followed by SN'type reaction of an intermediate 4 with additive nucleophiles to give 1-substituted carbazole sulfides 2.

📜 SIMILAR VOLUMES

ChemInform Abstract: Unusual Cyclization
ChemInform Abstract: Unusual Cyclization and SN′-Type Displacement of Carbazole Sulfoxide under Pummerer Reaction Conditions.
✍ T. KAWASAKI; H. SUZUKI; I. SAKATA; H. NAKANISHI; M. SAKAMOTO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB

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