Abstract
Abstract Olefins underwent dehydrogenative 1,2- and/or 1,1-double silylation with o-bis(dimethylsilyl)benzene (1) in the presence of a catalytic amount of Pt(CH2CH2)PPh3)2 to afford benzo-1,4-disilacyclohexene (3) and/or benzo-1,3-disilacyclopentene (4) derivatives, respectively. In reactions of aliphatic olefins, single hydrosilylation with one of the SiH bonds took place as a side reaction to give HMe2Si(o-C6H4)SiMe2R compounds. Depending on the conditions of the latter reactions, HMeRSi(o-C6H4)SiMe3 compounds arising from 1,4-rearrangement of a methyl group were also formed. The cyclic bis(silyl)platinum complex Me2 Si(o-C 6 H 4 )SiMe 2 P t(PPh3)2 (11) formed upon treatment of 1 with the platinum-ethylene complex readily reacted with olefins in the presence of 1 to afford 3 and/or 4. Compound 4 coming from the catalytic reaction of styrene with o-bis(deuteriodimethylsilyl)benzene did not have the deuterium label incorporated. Based on these results, the dehydrogenative double silylation is proposed to take place via 11 as a key intermediate.
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