The Allylic Azide Rearrangement: Achieving Selectivity
Journal of the American Chemical Society2005Vol. 127(39), pp. 13444–13445
Citations Over TimeTop 14% of 2005 papers
Abstract
Allylic azides undergo a rapid [3.3]-sigmatropic rearrangement which results in dynamic equilibrium of several isomers. Thus, reactions of allylic azides usually result in mixtures of products. However, even small differences in reactivity of the isomeric allylic azides can be amplified to result in a single product in good to excellent yields. For example, the Cu(I)-catalyzed cycloaddition with alkynes selectively captures primary and secondary allylic azide isomers, whereas MCPBA epoxidation favors isomers which contain more electron-rich double olefins.
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