Weak carbon-carbon bonds. Synthesis, structure, and reactions of 7-Methyl-1,3,5-triphenyl-2,4,9-trithia-1,3,5-tristannaadamantane

Article abstract of DOI:10.1021/om00093a026

7-Methyl-1,3,5-triphenyl-2,4,9-trithia-1,3,5-tristannaadamantane (1-CH₃) was synthesized to test the possibility that a carbon-methyl bond activated by three antiperiplanar carbon-tin bonds might be a reactive donor of methyl. MNDO calculations suggest that the strength of the carbon-methyl bond in compound 1-CH₃ should be about 40 kcal/mol. Nevertheless, the reactivity of this bond is not conspicuously high. This is presumably because the methyl group is neopentylic and sterically hindered and because other weak bonds in compound 1-CH₃ are even more reactive and obscure the intrinsic activation of the carbon-methyl bond by making reactions occur elsewhere.