Cyclobutadiene to Tetrahedrane: Valence Isomerization Induced by One-Electron Oxidation

A new procedure for synthesizing tetrakis(trimethylsilyl)tetrahedrane from tetrakis (trimethylsilyl)cyclobutadiene is reported. Valence isomerization of cyclobutadiene to tetrahedrane induced by one-electron oxidation has been developed by the addition of tris(pentafluorophenyl)borane as an oxidant. This new method has great synthetic advantages for easy, quick, and high-yielding reaction to achieve gram-order-scale synthesis of tetrakis (trimethylsilyl)tetrahedrane. (C) 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:412-416, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20699