Rearrangement of hindered phenols containing silicon or germanium
Shielded phenols containing silicon and/or germanium have been found to rearrange to phenoxysilanes or phenoxygermanes under the influence of complex formation with oxygen.
The silicon- and germanium-containing phenols form π complexes with oxygen in which the oxygen acts as an acceptor. The constants of complex formation have been determined.
Silicon- and germanium-containing shielded phenols, when exposed to elevated temperatures or the action of bases, rearrange to phenoxysilanes or phenoxygermanes. The germanium-containing phenols are more stable at high temperatures than are the silicon-containing phenols, but are rearranged more readily under the influence of organic bases. The p isomers are more stable than the o isomers.
KeywordsOxygen Silicon Phenol Elevated Temperature Complex Formation
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