Copper-Catalyzed Ritter-Type Reaction of Unactivated Alkenes with Dichloramine-T

✍ Scribed by Takumi Abe; Hiroyuki Takeda; Yoshihisa Miwa; Koji Yamada; Reiko Yanada; Minoru Ishikura

• Book ID: 102253755
• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 191 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200900214

✦ Synopsis

Abstract

It was shown that dichloramine‐T (1) reacted with cyclohexene in acetonitrile to give N^1^‐(2‐chlorocyclohexyl) amidine 2a and N‐(2‐chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N‐chloro‐N‐tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)~2~, primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.