Acid-catalyzed isomerization of substituted indenes : attempted synthesis of indenylacetone from prop-2-ynylindene
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 6,p. 944-947
- https://doi.org/10.1039/j39690000944
Abstract
Hydration of 3-prop-2-ynylindene gave a substantial quantity of 1-acetonylideneindane (III). The isomerization of the double bond from the five-membered ring of indene to the exo-position is explained in terms of an equilibrium between acetonylindene (II) and 1-acetonylideneindane (III); this isomerization was catalyzed by acids. A similar equilibrium was found in the acid-catalyzed isomerization of 3-benzylindenes C9H7·CH2Ph C9H8 CHPh. Both steric and conformational effects were shown to influence this equilibrium very strongly.Keywords
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