One-Shot Double Amination of Sondheimer鈥揥ong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes

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• 作者：Feng Xu ; Lifen Peng ; Kenta Shinohara ; Takanori Nishida ; Kan Wakamatsu ; Motoyuki Uejima ; Tohru Sato ; Kazuyoshi Tanaka ; Norihiko Machida ; Haruo Akashi ; Akihiro Orita ; Junzo Otera
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：17
• 期：12
• 页码：3014-3017
• 全文大小：338K
• ISSN：1523-7052

文摘

Photoluminescent diamino-substituted dinaphthopentalenes were synthesized successfully by the treatment of in situ prepared dinaphthocyclooctadiyne with lithium amide. This reaction involves a series of transformations including the nucleophilic addition of the lithium amide to a triple bond of the cyclooctadiyne moiety, transannulation, protonation of the resulting pentalene anion, and the nucleophilic substitution of the pentalene core with the lithium amide. In this procedure, a novel double amination step plays a key role. When the diamino-substituted dinaphthopentalenes were irradiated with UV light in toluene, fluorescence was observed at around 580 nm (桅_F < 0.03).