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

Feng Xu, Lifen Peng, Kenta Shinohara, Takanori Nishida, Kan Wakamatsu, Motoyuki Uejima, Tohru Sato, Kazuyoshi Tanaka, Norihiko Machida, Haruo Akashi, Akihiro Orita, Junzo Otera

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

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 (φF < 0.03).

Original languageEnglish (US)
Pages (from-to)3014-3017
Number of pages4
JournalOrganic Letters
Volume17
Issue number12
DOIs
StatePublished - Jun 19 2015

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