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  Synthesis of α-nitro carbonyls via nitrations in flow

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002B-5262-6 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-5984-1
Genre: Journal Article

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 Creators:
Chentsova, Anna1, Author              
Ushakov, Dmitry B.1, Author              
Seeberger, Peter H.2, Author              
Gilmore, Kerry1, Author              
Affiliations:
1Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863304              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 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.

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 Dates: 2016-09-062016
 Publication Status: Published in print
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 Identifiers: DOI: 10.1021/acs.joc.6b01634
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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 81 (19) Sequence Number: - Start / End Page: 9415 - 9421 Identifier: ISSN: 0022-3263