Regio- and stereo-specific addition of organotellurium trihalides to ferrocenylacetylene: molecular and crystal structure of (Z)-halovinyl organotellurium dihalides

Abstract

Organotellurium(IV) trihalides RTeX₃ (X = Br, I) reacts readily with ferrocenylacetylene to give (Z)-products of electrophilic addition to C-C triple bond: (Z)-FcXC = CTeX₂R (R = Ph, X = Br (1) or I (2); R = trans-8-ethoxy-4-cyclooctenyl, X = Br). In case of PhTeX₃(X = Br or I) the room temperature reaction is spontaneous and the structure of the product does not depends on the polarity of the solvent used; this is in contrast to the reaction of aryl-acetylenes with RTeBr₃ which were reported to afford (E)-bromovinyl aryltellurium dibromides in methanol and its (Z)-isomer in benzene. Molecular and crystal structures of new compounds and effect of bulky and electron-rich ferrocenyl substituent on the reactivity of acetylene moiety are discussed in this paper.