Add time:07/29/2019         Source:sciencedirect.com

Four new (chloromethyl)disilanes, (ClCH2)Cl2SiSiCl2Me (I), (Cl2CH)Cl2SiSiCl2Me(II), (ClCH2)MeClSiSiClMe2(III) and (ClCH2)Me2SiSiCl3(IV), have been prepared and studied as to their attitude toward intramolecular rearrangement with aluminum chloride. The reactivity decreases in the order: (III) > (IV) > (II) ⪢ (I). Similar reactivity to rearrangement of Me3SiSiMe2(CH2Br)(V), ClMe2SiSiMe2(CH2Br) (VI) and Me3SiSiMeCl(CH2Br) (VII) in the presence of aluminum bromide has been found to decrease in the order: (V) > (VI) > (VII). The results are discussed in terms of a mechanism favoring initial rate-determining step of ionization of the carbon-halogen bond in which the migrating group plays a minor role, if any, followed by migration of a silyl group from silicon to carbon. Disilanes (I) and (II) enter into the Friedel-Crafts reaction with benzene to give, after methylation, PhCH2SiMe2SiMe3 and Ph2CHSiMe2SiMe3, respectively.

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