Detection and follow‐up reactions of distonic        <fi >β</fi>β        ,        <fi >β</fi>β        ‐dimesityl enol radical cations containing nitrogen heterocyclic bases

Cinar M. Emin; Lal Mukul; Deiseroth Hans‐J?rg; Schlirf Jens; Schmittel Michael

摘要

Abstract > β , β ‐Dimesityl enols E2 ‐ E4 containing various nitrogen heterocyclic bases in the α ‐position were investigated by laser flash photolytic oxidation and density functional theory in order to identify distonic enol radical cations in solution and characterize their immediate follow‐up reactions. Enol E1 with a tert ‐butyl group in the α ‐position served as a reference. Experimental and computational efforts reveal that one‐electron oxidation of enol E1 furnishes the enol radical cation, whereas oxidation of E2 ‐ E4 provides distonic radical cations in solution. While the distonic radical cations of E2 ‐ E3 undergo intermolecular acid‐base reactions, the distonic radical cation of E4 experiences an intramolecular hydrogen abstraction followed by subsequent ring closure and ring‐opening steps. As a final product on the laser flash photolysis time scale, the rearranged radical cation E4d ‐ R is generated that is characterized by a dimesitylmethyl radical subunit. </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 Type =“main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > β</ i>，β</ i> -dimesityl通过激光闪光光解氧化和密度泛函理论研究了含有各种氮杂环碱的烯醇 - e4 </ b>含有各种氮杂环基碱基，以识别溶液中的倾斜烯醇激进阳离子并表征其即时后续反应。烯醇 e1 </ b>在α</ i>中的 tert </ i> - 丁基作为参考。实验和计算努力揭示了烯醇 e1的单电子氧化，提供烯醇自由基阳离子，而 E2的氧化，e2 - e4 </ b>提供了扩张自由基阳离子在解决方案中。虽然 e2 </ b> - e3 / b>的延伸自由基阳离子经历分子间酸碱反应，但是 e4的横差阳离子经历分子内氢抽取之后的经历随后的环形封闭和开环步骤。作为激光闪光光解时间标度的最终产物，产生重排泌阳离子<B> E4D </ B> - <B> R </ B>，其特征在于二贝甲基自由基亚基。 </ 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-35546/'>《Journal of Physical Organic Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第11期</span><b style="margin: 0 2px;">|</b><span>共10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=Cinar M. Emin&option=202" target="_blank" rel="nofollow">Cinar M. Emin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lal Mukul&option=202" target="_blank" rel="nofollow">Lal Mukul;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Deiseroth Hans‐J?rg&option=202" target="_blank" rel="nofollow">Deiseroth Hans‐J?rg;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Schlirf Jens&option=202" target="_blank" rel="nofollow">Schlirf Jens;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Schmittel Michael&option=202" target="_blank" rel="nofollow">Schmittel Michael;</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>Department Chemie‐BiologieUniversit?t SiegenSiegen Germany;</p> <p>Department Chemie‐BiologieUniversit?t SiegenSiegen Germany;</p> <p>Department Chemie‐BiologieUniversit?t SiegenSiegen Germany;</p> <p>Department Chemie‐BiologieUniversit?t SiegenSiegen Germany;</p> <p>Department Chemie‐BiologieUniversit?t SiegenSiegen Germany;</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/4796.html" title="有机化学一般性问题">有机化学一般性问题;</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=cyclic voltammetry ( CV )&option=203" rel="nofollow">cyclic voltammetry ( CV );</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=density functional theory ( DFT )&option=203" rel="nofollow">density functional theory ( DFT );</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=distonic radical cation&option=203" rel="nofollow">distonic radical cation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=laser flash photolysis ( LFP )&option=203" rel="nofollow">laser flash photolysis ( LFP );</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=enol radical cation&option=203" rel="nofollow">enol radical cation;</a> </p> <div class="translation"> 机译：循环伏安法（CV）;密度函数理论（DFT）;扩展自由基阳离子;激光闪光光解（LFP）;ENOL自由基阳离子; </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/0704025793695.html">Detection and follow‐up reactions of distonic <fi >β</fi>β , <fi >β</fi>β ‐dimesityl enol radical cations containing nitrogen heterocyclic bases</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cinar M. 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Detection and follow‐up reactions of distonic ββ , ββ ‐dimesityl enol radical cations containing nitrogen heterocyclic bases

摘要