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Issue 12, 2016
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On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes

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Abstract

In this work, rearrangement reactions subsequent to the oxidation of tertiary amines were studied in 2-(cyanoethyl)-2-azanorbornane/ene systems. [1,2]- and [2,3]-Meisenheimer rearrangements, as well as the Cope elimination reaction, were observed with virtually complete selectivity. It was found that 2-(cyanoethyl)-2-azanorbornanes afford N-hydroxylamines through Cope elimination reactions and 2-(cyanoethyl)-2-azanorbornenes are prone to Meisenheimer rearrangements. In addition, the endo/exo configuration of 2-azanorbornenes plays a key role in the Meisenheimer rearrangement outcome. All the synthesized compounds were fully characterized by NMR spectroscopy and HRMS.

Graphical abstract: On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes

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Publication details

The article was received on 04 Jul 2016, accepted on 09 Sep 2016 and first published on 10 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00330C
Citation: Org. Chem. Front., 2016,3, 1624-1634
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    On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes

    C. A. D. Sousa, I. E. Sampaio-Dias, X. García-Mera, C. F. R. A. C. Lima and J. E. Rodríguez-Borges, Org. Chem. Front., 2016, 3, 1624
    DOI: 10.1039/C6QO00330C

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