Facile synthesis of functionalized lactones and organocatalytic ring-opening polymerization

Abstract

A facile one-step synthesis of functionalized valerolactones was carried out by the conjugate addition of thiols to the α,β-unsaturated valerolactone 5,6-dihydro-2Hpyran-2-one. The resultant 3-mercaptovalerolactones undergo ring-opening polymerization in solution or in the melt to generate polyesters functionalized either with benzyl mercaptans or oligoethylene glycol pendant groups. The copolymerization of the 3-mercaptovalerolactones with ε-caprolactone generates random copolymers. © 2012 American Chemical Society.