Catalyst-free depolymerization of polycaprolactone to silylated monoesters and iodide derivatives using iodosilanes
Résumé
The homogeneous depolymerization of polycaprolactone (PCL) with excess iodotrimethylsilane (Me3SiI) proceeds without catalysts and selectively afforded I(CH2)5CO2 SiMe3 or a mixture of I(CH2)5-CO2 SiMe3 and I(CH2)5CO 2I depending on the solvent (CH2Cl2, MeCN). The latter mixture can undergo methanolysis or hydrolysis into the valuable ester I(CH2 5CO2Me or the acid I(CH2) 5CO2H. In contrast, SiH2 I2 depolymerized PCL into the fully deoxygenated species I(CH2) 6I and n-hexane.
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