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.
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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