Stereochemistry of the Elimination of Norcamphor- and Apocamphor Tosylhydrazone with Methyllithium†
作者： Kwang-Ting Liu , Robert H. Shapiro
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摘要: Upon treatment with three equivalents of methyllithium in ether at room temperature exo-3-d-norcamphor tosylhydrazone gave norbornene which retained 21% the deuterium and exo-3-d-apocamphor apobornylene 50% based on nmr mass spectral analysis. In both cases exo-elimination is favored when primary isotope effect considered. The relatively low selectivity between exo-and endo-elimination as compared that observed solvolytic studies was tentatively rationalized by carbarion character transition state leading to proton abstraction base.
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