Collect. Czech. Chem. Commun.
1989, 54, 3088-3091
https://doi.org/10.1135/cccc19893088
Titanium-catalyzed Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene
Karel Macha, Helena Antropiusováa, Vladimír Hanuša and Petr Sedmerab
a The J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 182 23 Prague 8
b Institute of Microbiology, Czechoslovak Academy of Sciences, 142 20 Prague 4
Abstract
The TiCl4-(C2H5)2AlCl catalyst induced the Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene affording 2,3-bis(trimethylsilyl)bicyclo[2.2.2]octa-2,5-diene in 72% yield under mild conditions. The product eliminates ethylene upon heating to 240 °C to give 1,2-bis(trimethylsilyl)benzene.
