The
preparation of a novel class of ε-caprolactone (CL) monomers,
modified at the β-position of the ester function, is described.
The efficient thia-Michael addition to cyclohex-2-en-1-one and subsequent
Baeyer–Villiger oxidation provided the regioselectively modified
CL monomers. To enable a sustainable Baeyer–Villiger oxidation,
several reaction procedures were investigated. In order to test a
controlled ring-opening polymerization of the prepared monomers, the
kinetics were studied and the monomer to initiator ratios were varied
in order to prepare poly(ε-caprolactone)s with different molecular
weights and different side groups.
Palladium nanoparticles,
stabilized by poly(vinylpyrrolidone) (PdNP@PVP), catalyze
the ring-opening of limonene dioxide (LDO)
with water. The use of PdNP@PVP selectively results in
the ring opening of the exo-cyclic epoxide to form 1. Contrarily, using different concentrations of only poly(vinylpyrrolidone)
(PVP) alone, a selectivity toward the exo-cyclic 1 or endo-cyclic epoxide ring-opening 2 was observed. Investigations revealed that this selectivity
is due to kinetic control of the reaction. The cis- and trans-LDO isomers showed different reactivities,
reacting to limonene-8,9-diol and limonene-1,2-diol, respectively.
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