1,3-Cyclohexadiene, 2,3-bis[(trimethylsilyl)oxy]-

Uses

1,3-Cyclohexadiene, 2,3-bis[(trimethylsilyl)oxy]- is useful for Diels-Alder reactions giving highly functionalized [2.2.2] bicyclic systems.

Preparation

1,3-Cyclohexadiene, 2,3-bis[(trimethylsilyl)oxy]- is prepared by the sequential silylation of 1,2-cyclohexanedione with a weak base and Trimethylsilyl Trifluoromethanesulfonate or under strongly basic conditions.

storage

silyl enol ethers are susceptible to hydrolysis under basic and especially acidic conditions or in the presence of fluoride ion and other silyl specific nucleophiles (e.g. DMSO, DMF). Precautions should therefore be adopted to protect such enol ethers from moisture.