Abstract
The solvolysis of 9-homocubyl triflate-9-d (8-9-d), the deamination of 9-homocubylammonium chloride-9-d (15-9-d), and most likely also the fluorodeiodination of 9-homocubyl iodide-9-d (13-9-d) take place in a highly stereoselective manner. Both deamination and solvolysis products have the deuterium label scrambled only over one face of the homocubul cage (syn to the substituent) and are formed with retention at C(6). In more nucleophilic media, the solvolysis of 8-9-d loses the stereoselectivity due to partial S N 2 substitution, and under nonionizing, very nucleophilic conditions, a pure S N 2 displacement of the triflate takes place
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