2,3,8,9-Dibenzo-5,6-(substituted)benzo-1,4-dithio-7-azacyclonona-2,5,8-trienes. Synthesis and mechanistic study

✍ Scribed by Kyongtae Kim; Man Nyoung Kim

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 717 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340101

✦ Synopsis

Abstract

5‐(2‐Acetamidoaryl)thianthreniumyl perchlorates reacted with potassium hydroxide in methanol at reflux giving 2,3,8,9‐dibenzo‐5,6‐(substituted)benzo‐1,4‐dithio‐7‐azacyclonona‐2,5,8‐trienes 4 in 43 to 75% yields, whereas the reactions of the same compounds with sodium hydride in the absence or in the presence of dimethyl sulfate in refluxing tetrahydrofuran gave N‐acetylated and N‐methylated 4 in 68 to 96% and 27 to 56% yields, respectively. The mechanism of the formation of the products might be explained by a nucleophilic attack of amide ions 10, 12, and 14 at the ipso‐position of the thianthrene ring. A sulfuranyl radical mechanism might be involved in these reactions.