Abstract
Vinylboranes derived from terminal and internal acetylenes via hydroboration with dicyclohexylborane undergo an instantaneous reaction with mercuric acetate at 0° to give the corresponding vinylmercury acetates. Treatment with aqueous sodium chloride provides a convenient stereospecific synthesis of vinylmercury chlorides. This reaction is accompanied by a “side reaction” leading to cyclohexyl olefins and elemental mercury. The extent of this “side reaction” is apparently determined by the steric requirements of the vinylborane. Greater than 85% isolated yields of isomerically pure trans-vinylmercury chlorides can be obtained from terminal acetylenes. The yields of isomerically pure cis-vinylmercury chlorides from internal acetylenes are somewhat lower.
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