Peptide-Polymer Conjugates as Model Systems To Explore the Functional Space of Precision Polymers

Brummelhuis, Niels ten; Wieczorek, Sebastian; Wilke, Patrick; Schwemmer, Thorsten; Börner, Hans G.

doi:10.1021/bk-2014-1170.ch004

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“…Alternating copolymers are of interest for a multitude of applications ranging from the biological to nanoelectronics and catalysis. − Generally, alternating copolymers have been synthesized by radical polymerization − and metal-mediated routes, including CO 2 /epoxide copolymerizations and catalyst transfer polymerizations of heterocycles . However, the introduction of functionality can be limited by reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Access to Bicyclo[4.2.0]octene Monomers To Explore the Scope of Alternating Ring-Opening Metathesis Polymerization

Chen

Sampson

2018

J. Org. Chem.

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Bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides undergo alternating ring-opening metathesis polymerization (AROMP) with cyclohexene. Herein, a general method for the preparation of bicyclo[4.2.0]oct-(8)-ene-8-carboxy derivatives is described. The central 8-cyano intermediate provides entry to five different functional group substituents on the alkene. These monomers were tested as potential substrates for AROMP with cyclohexene. In addition to the carboxamide, the carboxynitrile and carboxaldehyde are also substrates for AROMP. In the case of the carboxaldehyde, the polymer is regioregular. However, the addition of carboxynitrile is stereoirregular and slow.

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