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Oxygen-mediated Polymerization Initiated by Oltipraz-derived Thiones.

Scott R Zavada¹, Joseph C Furgal², Nathan D Wood²

¹Macromolecular Science and Engineering Program, University of Michigan, Ann Arbor, MI 48109-2136, USA.

Journal of Polymer Science. Part A, Polymer Chemistry

|September 27, 2017

Summary

This study explores using a pyrrolopyrazine-thione as an initiator for radical polymerization. While it generates radicals, side reactions limit polymerization success due to complex chemical interactions.

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Area of Science:

Polymer Chemistry
Organic Synthesis

Background:

Oltipraz derivatives are known chemopreventive agents.
Pyrrolopyrazine-thiones can generate radicals via redox cycling with thiols and oxygen.
Radical-mediated thiol-ene polymerization is a valuable synthetic tool.

Purpose of the Study:

To investigate the use of an in situ generated pyrrolopyrazine-thione as an initiator for radical-mediated thiol-ene polymerization.
To understand the factors influencing the efficiency of this polymerization system.

Main Methods:

In situ generation of pyrrolopyrazine-thione from a precursor.
Initiation of radical-mediated thiol-ene polymerization.
Analysis of reaction extents and identification of side reactions.

Main Results:

Pyrrolopyrazine-thione successfully generated radicals in the presence of thiols and oxygen.
Achieved reaction extents were limited by undesired side reactions that quenched radical production.
Complex interactions between the initiator, precursor, oxygen, and thiols were identified as critical factors.

Conclusions:

Pyrrolopyrazine-thione shows potential as an oxygen-mediated polymerization initiator.
Optimization is needed to overcome side reactions and enhance polymerization efficiency.
Understanding the intricate reaction network is key to successful application.