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Issue 30, 2012
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The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes

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Abstract

1,6-Enynes with electron-donating substituents at the alkyne undergo gold(I)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale for these effects, and suggest that bicyclo[3.2.0]hept-5-enes are involved as intermediates. We provide the first X-ray structural evidence for the formation of a product of this class in a cycloisomerisation of a 1,6-enyne.

Graphical abstract: The role of cyclobutenes in gold(i)-catalysed skeletal rearrangement of 1,6-enynes

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Publication details

The article was received on 27 Feb 2012, accepted on 02 May 2012 and first published on 03 May 2012


Article type: Paper
DOI: 10.1039/C2OB25419K
Citation: Org. Biomol. Chem., 2012,10, 6105-6111
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    The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes

    A. Escribano-Cuesta, P. Pérez-Galán, E. Herrero-Gómez, M. Sekine, A. A. C. Braga, F. Maseras and A. M. Echavarren, Org. Biomol. Chem., 2012, 10, 6105
    DOI: 10.1039/C2OB25419K

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