Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers.

ABSTRACT: Naturally occurring safrole I upon epoxidation gave safrole oxide II, which underwent ring opening polymerization using a Lewis acid initiator/catalyst comprising of triphenylmethylphosphonium bromide/triisobutylaluminum to afford new polyether III in excellent yields. Epoxy monomer II and allyl glycidyl ether IV in various proportions have been randomly copolymerized to obtain copolymer V. A mechanism has been proposed for the polymerization reaction involving chain transfer to the monomers. A strategy has been developed for the deprotection of the methylene acetal of V using Pb(OAc)₄ whereby one of the methylene protons is replaced with a labile OAc group to give VI. The pendant allyl groups in VI have been elaborated via a thiol-ene reaction using cysteamine hydrochlor

SUBMITTER: Alhaffar MT 

PROVIDER: S-EPMC9066001 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature