Alkoxides organomercuries

This route has, for example, been used to make the butyl compounds.15 The trimethylsilylmethyl derivatives have also been made1617 they can be precipitated from cyclohexane, washed free from organomercury starting materials, and obtained without organometal-alkoxide contaminants. Alternatively, KCH2SiMe3 may be used in situ, e.g., for metallation of alkenes.18... 

Ethers are prepared either by a Williamson synthesis or by alkoxymercuration/demercuration sequence. The Williamson ether sy thesis involves S -2 attack of an alkoxide ion on a primary alkyl halide. The alkoxymercuration reaction involves the formation of an intermediate organomercury compound, followed by NaBH4 reduction of the C-Hg bond. The net result is Markovnikov addition of an alcohol to an alkene. 

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See also in sourсe #XX -- [ , , , , ]

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