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. 2023 Jun 19;62(25):e202303375.
doi: 10.1002/anie.202303375. Epub 2023 May 9.

Head-to-Tail Dimerization of N-Heterocyclic Diazoolefins

Paul Varava  1 , Tak Hin Wong  1 , Zhaowen Dong  2 , Anastasia Yu Gitlina  1 , Andrzej Sienkiewicz  3   4 , Wolfram Feuerstein  1 , Rosario Scopelliti  1 , Farzaneh Fadaei-Tirani  1 , Kay Severin  1
Affiliations

Head-to-Tail Dimerization of N-Heterocyclic Diazoolefins

Paul Varava et al. Angew Chem Int Ed Engl. .

Abstract

The head-to-tail dimerization of N-heterocyclic diazoolefins is described. The products of these formal (3+3) cycloaddition reactions are strongly reducing quinoidal tetrazines. Oxidation of the tetrazines occurs in a stepwise fashion, and we were able to isolate a stable radical cation and diamagnetic dications. The latter are also accessible by oxidative dimerization of diazoolefins.

Keywords: Cycloaddition; Diazo Compound; Diazoolefin; Redox Activity; Tetrazine.

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