Unsaturated Acyl Derivatives of Silicon, Germanium, and Tin from Metalated Enol Ethers

Article abstract of DOI:10.1021/ja00525a019

The preparation of 1-lithio derivatives of some conjugated vinyl ethers is described.Reaction of these compounds with the chlorotrimethyl derivatives of silicon, germanium, and tin gives the corresponding metallovinyl ethers in 50-80percent yield.At least in the case of silicon these reactions proceed with retention of stereochemistry.The silyl compounds undergo Z <*> E photoisomerization.Hydrolysis of the ethers in aqueous acetone gives the corresponding acylmetallanes in 60-75percent yield.The metalation and hydrolysis reactions are examined in some detail.The spectral properties of these novel unsaturated acylmetallanes are presented and discussed.