Reactions of compounds containing SnLi and GeLi bonds with organic and organometallic peroxides

The reactions of tris(trimethylsilylmethyl)stannyllithium, tris(trimethylsilylmethyl)germyllithium and triethylgermyllithium with di-t-butyl peroxide, bis(trimethylsilyl)peroxide, trimethyl(t-butylperoxy)silane, triphenyl(t-butyl-peroxy)germane, bis(triphenylgermyl) peroxide, triphenyl(trimethylsilylperoxy)-germane, benzoyl peroxide and dicyclohexyl peroxydicarbonate were investigated. The reactions proceed under mild conditions with nucleophilic attack by the R₃M anion (R = Et, Me₃SiCH₂, M = Ge, Sn) on one of the peroxide oxygen atoms. In the case of unsymmetrical organometallic peroxides the character of nucleophilic cleavage is dependent on the nature of the starting nucleophile, steric effects of peroxide group substituents and other factors.