Synthesis of monomers for radical ring opening polymerization

CHED 825

Truong Vo, kaubrech@holycross.edu, Department of Chemistry, College of the Holy Cross, 1 College Street, Worcester, MA 01610 and Katherine B. Aubrecht, tvo08@holycross.edu, Deparment of Chemistry, College of the Holy Cross, 1 College Street, Worcester, MA 01610.
We seek to make novel biodegradable polymers by copolymerizing alkyl methyacrylates with monomers that undergo radical ring opening polymerization (RROP). We are targeting two monomers with exocyclic double bonds, 1, and 2. We anticipate the ring strain from a seven-membered ring will encourage ring opening. The presence of both an electron donating and an electron withdrawing group will help to stabilize the propagating free radical. We expect that the presence of a benzylic position to also increase the stability of the ring-opened radical. We have prepared the saturated analog of 1 from 2-butenoxy propanoic acid via an iodolactonization. Progress towards 2 has been made by carrying out the alkylation of a mono-protected hydroxybenzyl alcohol with 2-bromopropionic acid. We are investigating methods for the lactonization of the deprotected product. We intend to introduce the exocyclic double bonds to the saturated analogs of 1 and 2 via free radical bromination and elimination.

 

Undergraduate Research Poster Session: Polymer Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Chemical Education

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007