Stereopopulation control: the apparent stabilization of a lactone to ring opening
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 7,p. 403
- https://doi.org/10.1039/c39720000403
Abstract
The lactone, 3,3,4,7-tetramethylphthalide, is completely resistant to ring opening by a variety of nucleophiles; since the carbonyl group is subject to 18O exchange, hydride reduction, and Grignard addition, the effect is not due to steric inaccessibility of the carbonyl, but to a rate of recyclization of the acyclic species so great that it escapes isolation.Keywords
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