Intramolecular Reactions of Oxindolyl Diazo Ketones

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Abstract
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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