Intramolecullar alkylation of phenols. Part 4. Base-catalysed cyclisation of phenolic enones. Scope and limitations
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1555-1566
- https://doi.org/10.1039/p19800001555
Abstract
The phenolic enones (4), (5), (8), (9), and (13) cyclise readily under acidic conditions. However, neither these nor the thin-substituted phenols (11a), (13a), (14a), and (15a) closed under basic conditions. Involvement of unfavourable equilibria is disproved. Comparison is made with related successful cyclisations of the saturated ketone (38) and aldehyde (39). Preliminary results suggest that strict stereo-electronic requirements are necessary for enone ring closure and that these conditions are not met in base-catalysed 5-Endo- and 6-Endo-Trigonal ring closures of the phenols of general type (2; n= 0 and n= 1).Keywords
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