A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) Å. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)2} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).

Graphical abstractAn unusual planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane, is reported. Its reaction with bis(1,5-cyclooctadiene)platinum(0) Pt(cod)2 gave 1,1′-bi-2-naphthol rather than the expected insertion products or polymer. Anionic ring-opening polymerization gave the corresponding poly(carbosilane).Figure optionsDownload full-size imageDownload as PowerPoint slide