Synthesis of a functionalized cyclic ester monomer

CHED 334

Kevin T. Petersen, ktpete06@holycross.edu, Department of Chemistry, College of the Holy Cross, 1 College Street, Worcester, MA 01610 and Katherine B. Aubrecht, jlrobe08@holycross.edu, Department of Chemistry, The College of the Holy Cross, 1 College Street, Worcester, MA 01610.
We report the synthesis of two monomers, 6-hydroxy hex-2-eneoic acid lactone and 6-hydroxy hex-3-enoic acid lactone. These two isomers are produce together through a two step synthesis beginning with 2-chloro-cyclohexanone reacting with (mCPBA) to get α-chloro-ε-caprolactone. α-chloro-ε-caprolactone was than reacted with toluene and diazobicyclononene to create the two products in a mixture. Further use of 6-hydroxy hex-3-enoic acid lactone has bi-functional polymerization characteristics. It will allow for a ring opening polymerization and after formation and the introduction of a radical initiator will allow for cross linking among polymers in a micelle. The cyclic ester monomer will be co-polymerized with capro-lactone. These polymers will form micelles once placed in an aqueous solution. Using a radical initiator on the double bonds we can cross link the polymers to form a more stable micelle structure.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Chemical Education

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006