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Synthesis of α-nitro carbonyls via nitrations in flow

MPS-Authors
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Chentsova,  Anna
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Ushakov,  Dmitry B.
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore,  Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Chentsova, A., Ushakov, D. B., Seeberger, P. H., & Gilmore, K. (2016). Synthesis of α-nitro carbonyls via nitrations in flow. The Journal of Organic Chemistry, 81(19), 9415-9421. doi:10.1021/acs.joc.6b01634.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-5262-6
Abstract
Reported is a safe, rapid method for the synthesis of α-nitro esters, via the trapping of nitronium ions. The two-stage nitration and subsequent deacetylation of readily available 1,3-dicarbonyl compounds was achieved using a biphasic semi-continuous approach. α-Nitro esters and amides were obtained in good overall yields (53–84%). Some of the α-nitro-1,3-dicarbonyl intermediates exhibit enhanced reactivity and undergo an acid-catalyzed Nef-type reaction to α-oxo-carbonyls.