Equimolar mixtures of trichlorovinylsilane and t-BuLi (1) were reacted with different vinyl ethers, CH 2 dCH-OR (R ) Et, n-Pr, n-Bu, i-Bu, t-Bu), to yield the silacyclobutanes 2-6. NMR spectroscopic investigations showed the addition of the formal silene unit Cl 2 Sid CHCH 2 t-Bu to the vinyl group of the vinyl ethers to be stereo-and regiospecific, forming products of E-configuration. In contrast, in the presence of bisvinyl [CH 2 dCH-O-(CH 2 ) n -O-CHdCH 2 (n ) 2, 4, 6)] or cyclic vinyl ethers, such as 2,3-dihydrofuran and 3,4-dihydro-2H-pyran, the formation of silacylobutanes was suppressed and the formation of addition and SiCl/CHLi coupling products, such as Cl 2 (R)SiCH 2 CH 2 t-Bu (RdCl, 7; t-Bu, 8) and the tetrachloro-1,3-disilacyclobutane, (Cl 2 SiCHCH 2 t-Bu) 2 (10), was favored. Compounds 8 and 10 were characterized by single-crystal X-ray diffraction studies.
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