Friday, July 20, 2018

organic chemistry - Neighbouring group participation with and without retention of configuration in nucleophilic substitution of 2,6-dichloro-9-thiabicyclo[3.3.1]nonane



Treatment of the dichloride A under the conditions indicated gives B with retention of configuration, while treatment of dichloride C gives D with inversion of configuration.


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I am having difficulty drawing out the inversion ring product to find out if the s lone pair can attack from anti to the $\ce{C-Cl}$ σ* bond on the vertical ring. If it does, then, there is retention of product in the first reaction after the $\ce{N3-}$ attacks.



Can someone please help using diagrams?




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periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

Apparently the of last four, $\ce{Mg^2+}$ is closest in radius to $\ce{Li+}$. Is this true, and if so, why would a whole larger shell ($\ce{...