Claisen rearrangement of tropolone ethers. Part III
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1960-1966
- https://doi.org/10.1039/p19730001960
Abstract
Pairs of allyl and prop-2-ynyl ethers derived from three 3-substituted tropolones have been prepared and structurally distinguished, and their thermal isomerisation products have been identified. Rearrangements of the 7-substituted tropolone ethers generally proceed via conventional [3,3] sigmatropic migration, but the 3-substituted isomers afford products resulting from both [3,3] and apparent [3,7] sigmatropic shifts, the proportion of each depending on the nature of the substituent. Kinetic evidence suggesting the operation of a direct [3,7] sigmatropic transfer has been obtained in the case of 3-bromo-2-(prop-2-ynyloxy)tropone.Keywords
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