Functionalization of polyisobutylene and polyisobutylene oligomers via the ritter reaction

Parada Corey M.; Storey Robson F.

摘要

ABSTRACT > The Ritter reaction, that is, reaction of a carbocation with a nitrile, was carried out on polyisobutylene (PIB) using a variety of reaction conditions. End quenching of PIB carbocations with acrylonitrile under living polymerization conditions (methyl chloride (MeCl)/hexane 60/40 (v/v) solvent mixtures at ?70?°C) resulted in either tert ‐chloride end groups or loss of chain‐end fidelity via carbocation rearrangement, as evidenced by NMR spectroscopy. Exo ‐olefin functionalized PIB substrates were also reacted with nitriles under a variety of reaction conditions including various acid and solvent medium combinations. In all cases, the result was either no reaction or PIB that had undergone severe backbone degradation, as determined via NMR spectroscopy and gel permeation chromatography. Finally, the Ritter reaction was performed on a series of exo ‐olefin functionalized oligoisobutylenes using acrylonitrile as the nitrile and either 60/40 dichloromethane/hexane or excess acrylonitrile as the solvent. In 60/40 dichloromethane/hexane, significant carbocation rearrangement and/or degradation resulted in a variety of isomeric, acrylamide‐functionalized oligomers. In excess acrylonitrile, the desired Ritter reaction was the only reaction observed, resulting in the smooth formation of the terminal acrylamide. The various N ‐oligoisobutylacrylamides thus obtained represent new hydrophobic monomers useful for the introduction of hydrophobic moieties into acrylamide‐based water‐soluble polymers. ? 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56 , 840–852 </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><abstract xmlns =“http://www.wiley.com/namespaces/wiley”type =“main”> <title type =“main”>抽象</ title> > ritter反应，即反应使用各种反应条件，在聚异丁烯（PIB）上对具有腈的碳粉区集。在活性聚合条件下用丙烯腈（甲基氯）/己烷60/40（v / v）溶剂混合物在α0℃）下的Pib碳酸酯的最终猝灭导致α0> tert </ i> - 氯化物末端通过碳粉算法重新排列，通过碳粉次分配重排组或丢失链终保真度，如NMR光谱所证明的。 Exo </ i> - 烯烃官能化Pib底物也与包括各种酸和溶剂培养基组合的各种反应条件下的腈反应。在所有情况下，结果是不经历严重的骨干劣化的反应或PIB，如通过NMR光谱和凝胶渗透色谱法测定的。最后，使用丙烯腈作为腈和60/40二氯甲烷/己烷或过量丙烯腈作为溶剂，在一系列官能化的寡替异亚丁基中进行裂解反应。在60/40二氯甲烷/己烷中，显着的碳分袋重排和/或降解导致各种异构，丙烯酰胺官能化的低聚物。在过量的丙烯腈中，所需的碎屑反应是唯一观察到的反应，导致酯丙烯酰胺的平滑形成。由此获得的各种 N </ i> - 醇异丁基丙烯酰胺代表了用于将疏水部分引入丙烯酰胺基水溶性聚合物的新型疏水性单体。还是2018 Wiley期刊，Inc.J.Colom。 SCI。，A部分：polym。化学。 2018 </ b>， 56 </ i>，840-852 </ p> </ abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-35621/'>《Journal of Polymer Science, Part A. Polymer Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第8期</span><b style="margin: 0 2px;">|</b><span>共14页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Parada Corey M.&option=202" target="_blank" rel="nofollow">Parada Corey M.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Storey Robson F.&option=202" target="_blank" rel="nofollow">Storey Robson F.;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>School of Polymer Science and EngineeringThe University of Southern Mississippi 118 College Drive #5050Hattiesburg Mississippi 39406;</p> <p>School of Polymer Science and EngineeringThe University of Southern Mississippi 118 College Drive #5050Hattiesburg Mississippi 39406;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1184.html" title="有机化学">有机化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polyisobutylene&option=203" rel="nofollow">polyisobutylene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ritter reaction&option=203" rel="nofollow">Ritter reaction;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=N ‐substituted acrylamide&option=203" rel="nofollow">N ‐substituted acrylamide;</a> </p> <div class="translation"> 机译：聚异丁烯;RICTRINT反应;N-丙烯酰胺; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704020726039.html">Functionalization of polyisobutylene and polyisobutylene oligomers via the ritter reaction</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Parada Corey M.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Parada Corey M.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Storey Robson F.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Storey Robson F. </a> <a href="/journal-foreign-35621/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Polymer Science, Part A. 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