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

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 (3)). 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.

Graphical abstractOrganotellurium(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 or I; 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)-isomers in benzene.Figure optionsDownload full-size imageDownload as PowerPoint slide