Isolation and reactivity of an elusive diazoalkene

Antoni, P. W.; Golz, C.; Holstein, J. J.; Pantazis, D. A.; Hansmann, M. M.

doi:10.1038/s41557-021-00675-5

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Isolation and reactivity of an elusive diazoalkene

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Pantazis, D. A.
Research Group Pantazis, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Antoni, P. W., Golz, C., Holstein, J. J., Pantazis, D. A., & Hansmann, M. M. (2021). Isolation and reactivity of an elusive diazoalkene. Nature Chemistry, 13(6), 587-593. doi:10.1038/s41557-021-00675-5.

Cite as: https://hdl.handle.net/21.11116/0000-0008-9B7B-0

Abstract

Most functional groups, especially those consisting of the abundant elements of organic matter—carbon, nitrogen and oxygen—have been extensively studied and only very few remain speculative due to their high intrinsic reactivity. In contrast to the well-explored chemistry of diazoalkanes (R₂C=N₂), diazoalkenes (R₂C=C=N₂) have been postulated in several organic transformations, but remain elusive long-sought intermediates. Here, we present a room-temperature stable diazoalkene, utilizing a dinitrogen transfer from nitrous oxide. This functional group shows dual-site nucleophilicity (C and N atoms) and features a bent C–C–N entity (124°) and a long N–N bond together with a remarkable low infrared absorption (1,944 cm^–1). Substitution of N₂ by an isocyanide leads to a vinylidene ketenimine. Furthermore, photochemically triggered loss of dinitrogen might proceed through a transient triplet vinylidene. We anticipate the existence of a stable diazoalkene functional group to pave an exciting avenue into the chemistry of low-valent carbon and unsaturated carbenes.