Synthesis and isolation of the stable diaryldibromodisilene, Bbt(Br)Si═Si(Br)Bbt, has been accomplished for the first time. The dibromodisilene underwent substitution reactions with organometallic reagents on the low-coordinated silicon atom to afford the corresponding substituted disilenes. Furthermore, the reaction of 1 with t-BuLi afforded the corresponding 1,2-diaryldisilyne, BbtSi≡SiBbt, the characters of which were revealed by spectroscopic and crystallographic analyses.

Synthesis and Reactions of a Stable 1,2-Diaryl-1,2-dibromodisilene: A Precursor for Substituted Disilenes and a 1,2-Diaryldisilyne

Publisher Summary Remarkable progress of the chemistry of disilenes seems to encourage building up the modern general theory of bonding, structure, and reactions applied for the heavier main-group element chemistry in the near future; the general theory should include the theory for organic chemistry as a special case. This chapter discusses present advances in novel synthetic methods for various types of stable disilenes. Stable disilenes and other unsaturated compounds of heavier group-14 elements show unique spectroscopic properties that cannot be easily obtained from organic compounds. Bonding and structures of disilenes have also been discussed in the chapter. For a detailed discussion on the structure of disilenes, it is helpful to understand the intrinsic difference in the bonding between disilene and ethylene. The chapter highlights reactions and mechanisms of disilenes. During the past decade, many new types of reactions have been found for novel types of disilenes such as cyclic and bicyclic disilenes and conjugated tetrasiladienes. Mechanistic studies have recently been performed on several fundamental reactions of disilenes both theoretically and experimentally, and have greatly deepened the understanding of their reaction pathways, their potential energy surfaces, the factors determining the rates and stereochemistry, and so on.

Progress in the Chemistry of Stable Disilenes

SiO in a complex: The first silanone that is stable at room temperature (3) is reported. The two-step synthesis involves carbonylation of the silylidyne complex 1 to give the chromiosilylene 2, followed by oxidation of 2 with N2 O. Silanone 3 features a polar, short SiO bond (1.526(3) A) to a trigonal-planar-coordinated silicon center and reacts with water to give the dihydroxysilyl complex.

Silicon-oxygen double bonds: a stable silanone with a trigonal-planar coordinated silicon center.

Some recent advances in the chemistry of silicon and its homologues in low coordination states

The reaction of R*2MeSi−SiX2X′ (X/X′ = Cl/Br, Br/Cl) with NaR* (R* = supersilyl SitBu3) leads, probably via the silylenes R*2MeSi−SiX, to the trans-configurated disilene (R*2MeSi)ClSi=SiCl(SiMeR*2), which could be isolated as orange-red crystals. According to an X-ray structure analysis, the central SiClSi=SiClSi framework of the disilene − the formation mechanisms of which are discussed − is planar. The Si=Si double bond is as short as 2.163(4) A and shows a band in the Raman spectrum at 589 cm−1. Due to its insolubility in organic solvents, no NMR spectra of the disilene in solution were obtained. The spatially overcrowded disilene is stable towards H2O, MeOH, HF, and NaR*. It melts at 228 °C with decomposition. Reduction of the disilene occurs with LiC10H8 in THF with formation of a reaction mixture containing a chlorine-free product that gives a low field 29Si NMR signal at δ = 91.5 (the region for unsaturated Si atoms). It transforms in solution with traces of oxygen into a substance which, according to mass spectrometry (chemical ionization), shows a mass for the disilyne R*2MeSi−Si≡Si−SiMeR*2 plus two oxygen atoms. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Synthesis, Structure and Dehalogenation of the Disilene RClSi=SiClR [R = (tBu3Si)2MeSi]

Chemistry of Stable Disilenes

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Chemistry of Stable Disilenes