Organopolymerization of Multifunctional Gamma-Butyrolactones

Research seminar abstract

The first successful polymerization of the naturally occurring, tri-functional Tulipalin B , or β-hydroxy-α-methylene-γ-butyrolactone (βHMBL) is established. N-Heterocyclic carbene (NHC) and phosphazene superbase catalysts have been found to effectively polymerize βHMBL into polymer products, despite its trifunctionality consisting of reactive hydroxyl and exo-methylene groups as well as a five-membered lactone ring.. Initial analysis of the resulting polymer products revealed rather complex structures originated from multiple mechanistic pathways. Subsequent studies using four substructures of βHMBL, including dihydrofuran-2(3H)-one (FO), 3-methylfuran-2(5H)-one (3-MFO), 5-methylfuran-2(5H)-one (5-MFO), and 3-(hydroxymethyl) furan-2(5H)-one (3-HMFO) revealed multiple reaction types involved in this polymerization, including conjugate Michael and oxa-Michael additions as well as ene-type reactions, enabled by proton transfer, and mechanistic crossovers between different pathways. This presentation will describe the efforts to understand such a complicated system involving multifunctional γ-butyrolactones.



Division(s): Materials

Speaker: Jing Tang

Speaker Institution: Colorado State University

Event Date: 04-28-2017

Event Time: 4:00 PM

Event Location: Chemistry A101

Mixer Time: 3:45 PM

Mixer Location: Chemistry B101E

Host: E. Chen