The Equilibrium Acidity of A 9,10-Dihydrosilaanthracene on the Degree of Aromaticity of a System with Tetracoordinate Silicon

Bickelhaupt, F.; Mourik, G.L. van

doi:10.1016/s0022-328x(00)88184-x

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Cited by 13 publications

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“…Bromination of 3 with NBS ( N -bromosuccinic imide) gave the corresponding bromosilane 4 , which could in principle be a precursor of 9-silaanthracene, 5 . However, attempted dehydrobromination of 4 using LDA (lithium diisopropylamide), n -BuLi, or t -BuLi was unsuccessful, probably due to the low acidity of the proton at the 10-position . Treatment of 4 with a “super base”, i .…”

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The First Stable 9-Silaanthracene

2001

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The first stable 9-silaanthracene, 5, bearing an efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), was successfully synthesized by the reaction of the corresponding silyl triflate, 7, with a 1.0 M amount of lithium diisopropylamide. The aromaticity of 5 is discussed on the basis of the NMR, UV/vis, and Raman spectra, X-ray structural analysis, and theoretical calculations.

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The First Stable 9-Silaanthracene

2001

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Highly Reactive Small‐Ring Monosilacycles and Medium‐Ring Oligosilacycles

Andō

Kabe

2009

Patai's Chemistry of Functional Groups

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Neutralization‐Reionization Mass Spectrometry and Matrix Isolation of Some 9‐Silaanthracenes

et al. 1991

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Neutralization‐reionization mass spectrometry of silaanthracene radical cations, which are generated from the 9,10‐dihydro‐9‐silaanthracenes 1, 3, 8 and 11 under electron‐impact conditions, indicates that silaanthracenes are stable molecues in the gas phase. Flash pyrolysis of the starting compounds mentioned above also yields the silaanthracenes 2, 4, and 10, which may be isolated in an argon matrix at 15 K and exhibit characteristic UV spectra.

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The Equilibrium Acidity of A 9,10-Dihydrosilaanthracene on the Degree of Aromaticity of a System with Tetracoordinate Silicon

Cited by 13 publications

References 20 publications

The First Stable 9-Silaanthracene

The First Stable 9-Silaanthracene

Highly Reactive Small‐Ring Monosilacycles and Medium‐Ring Oligosilacycles

Neutralization‐Reionization Mass Spectrometry and Matrix Isolation of Some 9‐Silaanthracenes

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