Steric hindrance as a mechanistic probe for olefin reactivity: Variability of the hydrogenic canopy over the isomeric adamantylideneadamantane/ …

R Rathore, SV Lindeman, CJ Zhu, T Mori…

Index: Rathore; Lindeman; Zhu; Mori; Schleyer; Kochi Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5106 - 5116

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Citation Number: 19

Abstract

Access to each CC face of adamantylideneadamantane (AA) and sesquihomoadamantene (SA) is hindered by the hydrogenic canopy consisting of four β-hydrogens; otherwise, these olefins have quite normal environments. X-ray crystallography and density functional (DFT) calculations show a 0.5 Å larger annular opening in the protective cover of AA than that in SA. This contributes to the remarkable differences in reactivity toward various reagents, ...

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