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Evidence for an umpolung type of [2+2] cycloaddition of 2-carbamoyl ketenes

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Abstract

Ketenes generated during the thermal decomposition of 5-[(N-aryl/alkylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones react with highly electrophilic iminium ions. The initial [2+2] cycloaddition product rearranges to 2-arylidene malonamide. Mechanistic aspects of the process are presented.

Graphical abstract: Evidence for an umpolung type of [2+2] cycloaddition of 2-carbamoyl ketenes

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Publication details

The article was received on 13 Mar 2017, accepted on 02 Jun 2017 and first published on 02 Jun 2017


Article type: Letter
DOI: 10.1039/C7NJ00830A
Citation: New J. Chem., 2017, Advance Article
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    Evidence for an umpolung type of [2+2] cycloaddition of 2-carbamoyl ketenes

    A. Zakaszewska, E. Najda-Mocarska and S. Makowiec, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ00830A

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