Double silylation of 1,4-bis(trimethylsilyl)butadiyne with disilanes using a palladium catalyst.
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Reaction of 1,4-bis(trimethylsilyl)butadiyne with polychlorodisilanes Si<SUB>2</SUB>Cl<I><SUB>x</SUB></I>Me<SUB>6−<I>x</I></SUB> in the presence of a palladium catalyst gives, after methylation, 1,1,4,4-tetrakis(trimethylsilyl)butatriene and/or 1,1,2,4-tetrakis(trimethylsilyl)-1-buten-3-yne selectively. Hydrogenation, hydrosilylation, and oxidation of the obtained butatriene were found to take place at C(1)=C(2) double bond exclusively. The regioselectivity is ascribed to the geminally substituted silyl groups which sterically direct the attack of electrophile and stabilize postulated radical intermediates.
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