engleski

Lithiation/Silylation of Ethyl 2-Alkyl-1-Trimethylsilylcycloprop-2-ene-1-Carboxylate. Experimental and Computational Study

The formation of novel trimethylsilyl-substituted allenes, including silyl ketene acetals incorporating an allenic moiety, by lithiation/silylation of ethyl 2-alkyl-1-trimethylsilylcycloprop-2-ene-1-carboxylate, is described. The reaction involves formation of silyl ketene acetal 3 (3a) which upon aqueous work-up gives diasteromeric allenes 4' (4'a) and 4'' (4''a). Becke3LYP/6-311+G** calculations were also carried out to provide geometries, energies and insights into the electronic structure of the proposed reaction intermediates.

trimethylsilyl-substituted allene; lithiation of cyclopropene; ring opening; silyl ketene acetal; DFT calculations

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