Oxymercu ration-demercuration

Of the methods we have seen for Markovnikov hydration of alkenes, oxymercu-ration-demercuration is most commonly used in the laboratory. It gives better yields than direct acid-catalyzed hydration, it avoids the possibility of reanangements, and it does not involve harsh conditions. There are also disadvantages, however. Organomer-curial compounds are highly toxic. They must be used with great care and then must be disposed of properly. 

Preparative Methods three methods of preparation have been reported (a) from the treatment of ethyl bromoacetate with zinc followed by the reaction with chlorotrimethylsUane and subsequent reduction of the resultant ethyl trimethylsUylacetate with lithium aluminum hydride or borane-tetrahydrofuran (eq 1) (b) from the hydroboration/oxidation or oxymercu-ration/ demercuration of vinyltrimethylsUane (eq 2) and (c) most conveniently, by the reaction of the Grignard reagent formed from (chloromethyl)trimethylsilane with paraformaldehyde (eq 3). ... 

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See also in sourсe #XX -- [ , , , ]

See also in sourсe #XX -- [ , , , ]

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