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 CCl σ* bond on the vertical ring. If it does, then, there is retention of product in the first reaction after the NX3X attacks.



Can someone please help using diagrams?




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

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