Abstract
(1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphor- ylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N─Se interactions, with N─Se interatomic distances of ca. 2.1 Å, which diminish the electrophilic character of the selenium atom.
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