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Synthesis 1992; 1992(3): 323-327
DOI: 10.1055/s-1992-26101
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Intramolecular Reactions of Oxindolyl Diazo Ketones

Ernest Wenkert* , Song Liu
  • *Department of Chemistry (0506), University of California-San Diego, La Jolla, California 92093, USA
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Publication History

Publication Date:
17 September 2002 (online)

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Diazomethyl ketones, prepared from Diels-Alder adducts of methyl oxindolylideneacetic acid ester (methyl 2-oxo-3(2H)-indolylideneacetate) and 1,3-butadiene as well as 1,3-cyclohexadiene by standard means, were decomposed over dirhodium tetraacetate, in the hope of carbon-hydrogen insertion leading to cyclopentanone formation. However, in every case studied the diazo ketone underwent interaction with the neighboring benzene ring, resulting in the creation of a norcaradiene.

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