The cross metathesis reactivities of alpha-methylene-gamma-butyrolactone and an alpha-methylene-delta-lactone have been investigated. alpha-Methylene-gamma-butyrolactone undergoes rapid and efficient olefin isomerization in the presence of second-generation metathesis catalysts. However, cross metathesis can be achieved with the additive 2,6-dichlorobenzoquinone. In contrast, the alpha-methylene-delta-lactone neither isomerizes nor couples under similar conditions.
Cross metathesis of alpha-methylene lactones II
gamma- and delta-lactones
Raju, R., Allen, L. J., Le, T., Taylor, C. D., & Howell, A. R. (2007). Cross metathesis of alpha-methylene lactones II: gamma- and delta-lactones. Organic Letters, 9(9), 1699-1701. https://doi.org/10.1021/ol070574+
Abstract
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