Double bond geometry

The Peterson reaction

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There are many reactions in organic chemistry in which an Me3Si group acts like a proton. Just as acidic protons are removed by bases, silicon is readily removed by hard nucleophiles which can promote an elimination reaction as shown above. The reaction is known as the Peterson reaction and involves the regioselective elimination of alcohols under acidic conditions to give alkenes. It is particularly useful for making double bonds where other elimination methods might give the wrong regioisomer or mixture of regioisomers.

I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063–2192.