Crystal Structure of a Stable Silabenzene and Its Photochemical Valence Isomerization into the Corresponding Silabenzvalene

Silylenes, Silenes, and Disilenes: Novel Silicon‐Based Reagents for Organic Synthesis?

“…[28,29] In particular, Ottosson has exemplified this concept in a recent report describing an isolable silenolate 10 a although, having a very long Si À C bond (1.926 ), this is probably better described by the alternative resonance structure 10 b. [32,33] Despite the increased stability offered by the gain in aromatic resonance energy these compounds still require steric protection, coordination by a transition metal (see Scheme 5), or further stabilisation through electron donation to the silicon atom to inhibit dimerisation. Whilst stable 1-silaallenes 11, have been known since 1993, [31] the first stable silaaromatics 12 and 13 were only reported by Okazaki, Tokitoh and co-workers in 1997 and 2000, respectively.…”

Kinetic Stabilization of Highly Reactive Species Bearing Heteroatoms

“…The structure of silabenzene 49 was determined by X‐ray crystallographic analysis . The ORTEP drawing is shown in Fig.…”

An Ab Initio Molecular Orbital Study of Valence Bond Isomers of Silabenzene and Phosphabenzene

“…18 Silabenzene and 1-methylsilabenzene have been identified in an argon matrix at 10 K. 15−17 1-{2,4,6-Tris[bis(trimethylsilyl)methyl]phenyl}-silabenzene recently was isolated in C 6 D 6 by Wakita and coworkers. 27 2,6-Bis(trimethylsilyl)-1,4-ditert-butyl-1-silabenzene survives only below −100 • C and is stabilized by the coordination of the solvent. 28 Silabenzene, a 6π -electron cyclic species involving Si C multiple bonds, long resisted attempts to demonstrate its existence conclusively by observation of any of its molecular state fingerprints.…”