Revisiting Hafner’s Azapentalenes : The Chemistry of 1,3- Bis(dimethylamino)-2-azapentalene

Meiszter, Enikő and Gazdag, Tamás and Mayer, Péter József and Kunfi, Attila and Holczbauer, Tamás and Sulyok-Eiler, Máté and London, Gábor (2024) Revisiting Hafner’s Azapentalenes : The Chemistry of 1,3- Bis(dimethylamino)-2-azapentalene. JOURNAL OF ORGANIC CHEMISTRY, 89 (9). pp. 5941-5951. ISSN 0022-3263

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Abstract

Stable azaheterocyclic derivatives of pentalene have been reported by the group of Hafner in the 1970s. However, these structures remained of low interest until recently, when they started to be investigated in the context of organic light-emitting diodes’ (OLEDs’) development. Herein, we revisit the synthesis of stable azapentalene derivative 1,3-bis- (dimethylamino)-2-azapentalene and further explore its properties both computationally and experimentally. Beyond the reproduction and optimization of some previously reported transformations, such as formylation and amine substitution, the available scope of reactions was expanded with azo-coupling, selective halogenations, and cross-coupling reactions.

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