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Issue 20, 2002
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5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

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Abstract

Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol−1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.

Graphical abstract: 5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

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Publication details

The article was received on 07 Aug 2002, accepted on 04 Sep 2002 and first published on 18 Sep 2002


Article type: Communication
DOI: 10.1039/B207729A
Citation: Chem. Commun., 2002, 2338-2339
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    5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

    C. T. Falzon, I. Ryu and C. H. Schiesser, Chem. Commun., 2002, 2338
    DOI: 10.1039/B207729A

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