Abstract
π-Electron compounds that include multiple bonds between silicon atoms have received much attention as novel functional silicon compounds. In the present paper, 1,2-bis(trimethylsilyl)-1,2-disilacyclohexene 1 was successfully synthesized as thermally stable yellow crystals. Disilene 1 was easily converted to the corresponding potassium disilenide 4, which furnished novel functionalized disilenes after the subsequent addition of an electrophile. Interestingly, two trimethylsilyl groups in 1 can be stepwise converted to anthryl groups. The novel disilenes derived from 1 were characterized by a combination of nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), elemental analyses, and X-ray single crystal diffraction analysis. The present study demonstrates that disilene 1 can serve as a unit of cis-1,2-dialkyldisilene.
Highlights
IntroductionHave received much attention over the last three decades [1,2,3]
Stable silicon compounds that include double bonds between silicon atomshave received much attention over the last three decades [1,2,3]
We found a novel route to a disilenide from a stable disilene under milder conditions [16]
Summary
Have received much attention over the last three decades [1,2,3] Because such silicon π-electron systems have an intrinsically higher π-orbital level and a narrower HOMO (highest occupied molecular orbital)–LUMO (lowest unoccupied molecular orbital) gap compared to those of the corresponding organic π-electron systems, extended π-electron systems that include the Si=Si double bond(s) should be anticipated to be unprecedented functional π-electron materials. In this context, the reactions of disilenide (a disilicon analogue of vinyl anion [R2 Si=SiR]− ) with electrophiles is one of the promising routes to introduce a functional group into the silicon π-electron systems [4,5,6,7,8,9]. The disilenide was generated from the reaction of a trimethylsilyl-substituted disilene and potassium t-butoxide [17] via selective cleavage of the
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