Synthesis, reactivity, electrochemical and crystallographic studies of diferrocenoyl diselenide and ferrocenoyl selenides

Abstract

Diacyl diselenide (8), diacyl selenide (9) and acyl selenol esters (10-12) incorporating the ferrocenoyl substituent have been synthesized from ferrocene carboxylic acid (13). The new compounds (8-10) have been characterized by multinuclear NMR (¹H, ¹³C, ⁷⁷Se), IR spectroscopy and electrospray mass spectrometry. All compounds (8-13) undergo a one electron reversible oxidation at significantly more positive potential than ferrocene. The structures of the diselenide and selenide (8 and 10) have been confirmed by single crystal X-ray diffraction. The absolute structure parameter of 8 indicates that it crystallizes in an enantiomerically pure form. The peroxidase-like activities of the diselenide (8) and selenides (9-12) have been determined by the thiol assay.