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

doi:10.1021/acs.orglett.5b01293

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

Chemistry (Twin Cities)

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18 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 (φ_F < 0.03).

Original language	English (US)
Pages (from-to)	3014-3017
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.5b01293
State	Published - Jun 19 2015

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© 2015 American Chemical Society.

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title = "One-Shot Double Amination of Sondheimer-Wong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes",

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).",

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

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T1 - One-Shot Double Amination of Sondheimer-Wong Diynes

T2 - Synthesis of Photoluminescent Dinaphthopentalenes

AU - Xu, Feng

AU - Peng, Lifen

AU - Shinohara, Kenta

AU - Nishida, Takanori

AU - Wakamatsu, Kan

AU - Uejima, Motoyuki

AU - Sato, Tohru

AU - Tanaka, Kazuyoshi

AU - Machida, Norihiko

AU - Akashi, Haruo

AU - Orita, Akihiro

AU - Otera, Junzo

PY - 2015/6/19

Y1 - 2015/6/19

N2 - 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).

AB - 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).

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

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