Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines

Valiarovskii, Maksim A.; Vorob’ev, Alexander V.; Agafonova, Anastasiya V.; Novikov, Mikhail S.

doi:10.3390/M2204

Open AccessCommunication

Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines

by

Maksim A. Valiarovskii

,

Alexander V. Vorob’ev

,

Anastasiya V. Agafonova

and

Mikhail S. Novikov

^*

Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya Nab., 199034 St. Petersburg, Russia

^*

Author to whom correspondence should be addressed.

Molbank 2026, 2026(4), M2204; https://doi.org/10.3390/M2204

Submission received: 9 June 2026 / Revised: 10 July 2026 / Accepted: 10 July 2026 / Published: 14 July 2026

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Abstract

Tertiary (2H-azirin-2-yl)ammonium salts were prepared from methyl 2-halo-3-aryl-2H-azirine-2-carboxylates and 1,4-diazabicyclo[2.2.2]octane in very good to excellent yields. Both iodide and bromide salts are stable enough in crystalline form to be stored in a freezer for up to several months. The structures of the obtained salts were confirmed by NMR spectroscopy and HRMS.

Keywords: 2H-azirine; 1,4-diazabicyclo[2.2.2]octane; nucleophilic substitution

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Valiarovskii, M.A.; Vorob’ev, A.V.; Agafonova, A.V.; Novikov, M.S. Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines. Molbank 2026, 2026, M2204. https://doi.org/10.3390/M2204

AMA Style

Valiarovskii MA, Vorob’ev AV, Agafonova AV, Novikov MS. Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines. Molbank. 2026; 2026(4):M2204. https://doi.org/10.3390/M2204

Chicago/Turabian Style

Valiarovskii, Maksim A., Alexander V. Vorob’ev, Anastasiya V. Agafonova, and Mikhail S. Novikov. 2026. "Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines" Molbank 2026, no. 4: M2204. https://doi.org/10.3390/M2204

APA Style

Valiarovskii, M. A., Vorob’ev, A. V., Agafonova, A. V., & Novikov, M. S. (2026). Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines. Molbank, 2026(4), M2204. https://doi.org/10.3390/M2204

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Synthesis of Azirinylammonium Salts via Alkylation of DABCO with 2-Halo-2H-azirines

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