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Oxygen-mediated Polymerization Initiated by Oltipraz-derived Thiones.
Journal of Polymer Science Part A: Polymer Chemistry ( IF 2.869 ) Pub Date : 2017-02-11 , DOI: 10.1002/pola.28507
Scott R Zavada 1 , Joseph C Furgal 2 , Nathan D Wood 2 , Timothy F Scott 1, 2
Affiliation  

A pyrrolopyrazine-thione derived from oltipraz, a compound that has been investigated as a chemopreventive agent, affords radicals in the presence of thiols and oxygen via a redox cycle, an attribute that suggests its suitability as an initiator for oxygen-mediated polymerization. Here, we explore the utilization of this pyrrolopyrazine-thione, generated in situ from a precursor, as an initiator for the radical-mediated thiol-ene polymerization. While the pyrrolopyrazine-thione was shown to be capable of generating radicals in the presence of atmospheric oxygen and thiol groups, the reaction extents achievable were lower than desired owing to the presence of unwanted side reactions that would quench radical production and, subsequently, suppress polymerization. Moreover, we found that complex interactions between the pyrrolopyrazine-thione, its precursor, oxygen, and thiol groups determine whether or not the quenching reaction dominates over those favorable to polymerization.

中文翻译:

由Oltipraz衍生的亚硫醚引发的氧介导的聚合反应。

衍生自oltipraz的吡咯并吡嗪-硫酮(一种已被研究用作化学预防剂的化合物)可通过氧化还原循环在巯基和氧存在下提供自由基,这表明其适合作为氧介导的聚合反应的引发剂。在这里,我们探索了从前体原位生成的吡咯并吡嗪-硫酮作为自由基介导的硫醇-烯聚合反应的引发剂的利用。尽管显示吡咯并吡嗪-硫酮能够在大气氧和硫醇基团的存在下产生自由基,但由于存在不想要的副反应,该反应会终止自由基的产生并随后抑制聚合,因此可达到的反应程度低于所需的反应程度。 。此外,我们发现吡咯并吡嗪-硫酮之间存在复杂的相互作用,
更新日期:2019-11-01
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