The tautomerization and ring closure in the Claisen rearrangement: A DFT study

Yamabe Shinichi; Yamazaki Shoko

摘要

Abstract > Elementary processes of the aromatic Claisen rearrangement were investigated by DFT calculations. First, rearrangements of four substrates Ph—O—CH <sub>2</sub> —CH?CH <sub>2</sub> [A], Ph—O—CH <sub>2</sub> —CH?CH(OMe) [B], Ph—O—CH <sub>2</sub> —CH?CH <sub>2</sub> ····BF <sub>3</sub> [C], and Ph—O—CH—CH?CH(OMe)····BF <sub>3</sub> [D] were examined. In these systems, the tautomerization is initiated by the intermolecular proton transfer involving the transient ion‐pair intermediate. An ignition‐propagation chain‐reaction mechanism in the tautomerization was suggested. For [A], the ( ortho ‐allyl phenol → α‐methyl‐dihydrobenzofuran (α‐methyl‐cumarane)) process was found to be ready and the product of the Claisen rearrangement seems to be the cumarane rather than the phenol. In [D] (activated both by the terminal methoxy group and by the BF <sub>3</sub> catalyst), not the [3,3]‐sigmatropic shift but the tautomerization is the rate determining step. Second, the parent system, Ph—O—CH <sub>2</sub> —CH?CH <sub>2</sub> , was investigated with (H <sub>2</sub> O) <sub> n </sub> ( n ?=?2, 4, 6, and 10) systematically. The tautomerization takes place by the proton transfer via the water dimer or trimer. Except n ?=?2, similar changes of Gibbs free energies were obtained from the ether substrate to the cumarane. </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”> <标题类型=“main”>抽象</ title> >通过DFT计算研究了芳香族分支重新排列的基本进程。首先，重排四个基板pH-O-CH <sub> 2 </ sub> -CH？ch <sub> 2 </ sub> [a]，pH-O-ch <sub> 2 </ sub> -ch ？CH（OME）[B]，pH-O-CH <sub> 2 </ sub> -ch？ch <sub> 2 </ sub>····bf <sub> 3 </ sub> [c]和pH-O-CH-CH？CH（OME）····BF <Sub> 3 </ sub> [D]被检查。在这些系统中，通过涉及瞬态离子对中间体的分子间质子转移来启动互变异。提出了互拓化中的点火繁殖链反应机制。对于[a]，发现（邻孔</ i> - allyl酚→α-甲基二氢苯并呋喃（α-甲基 - 二氢苯甲酸））是准备好的，并且克兰森重排的产物似乎是含量的而不是苯酚。在[D]（通过终端甲氧基和BF和BF <sub> 3 </ sub>催化剂活化），不是[3,3] - 倍异性移位，但互变异化是速率确定步骤。其次，母体系统，pH-O-CH <sub> 2 </ sub> -ch？ch <sub> 2 </ sub>，（h <sub> 2 </ sub> o）<sub> n </ i> </ sub>（ n </ i>？=？2,4,6和10）系统地。通过水二聚体或三聚体通过质子转移进行互变异物。除了 n </ i>？2，从醚基质到含量碱中获得Gibbs自由能的类似变化。 </ 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-21753/'>《International Journal of Quantum Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第18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=Yamabe Shinichi&option=202" target="_blank" rel="nofollow">Yamabe Shinichi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yamazaki Shoko&option=202" target="_blank" rel="nofollow">Yamazaki Shoko;</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 of ChemistryNara University of EducationTakabatake‐cho Nara 630‐8528 Japan;</p> <p>Department of ChemistryNara University of EducationTakabatake‐cho Nara 630‐8528 Japan;</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/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</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=Claisen rearrangement&option=203" rel="nofollow">Claisen rearrangement;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=DFT calculations&option=203" rel="nofollow">DFT calculations;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=proton transfer&option=203" rel="nofollow">proton transfer;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=tautomerization&option=203" rel="nofollow">tautomerization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=transition states&option=203" rel="nofollow">transition states;</a> </p> <div class="translation"> 机译：Claisen重排;DFT计算;质子转移;互变化;过渡状态; 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tuijian_authcolor"> . 唐作华</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=周红平&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,周红平</a> <span> <a href="/journal-cn-12046/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学物理学报 </a> </span> <span> . 1994</span><span>,第003期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-3076_thesis/02022699850.html">有机化学中Claisen和联苯胺重排反应的周环机理</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=许家喜&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 许家喜</a> <span> <a href="/conference-cn-3076/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2014年高校化学化工课程教学系列报告会 </a> <span> <span> . 2014</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315600276.html">MBH酯参与构建四氢吡啶结构和烷氧基化/Claisen重排反应研究及天然产物Cortistatin A的合成探索</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=魏剑&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 魏剑</a> <span> . 2018</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120114032108.html">一种在较低温度下催化Claisen重排的方法</a> <b>[P]</b> . <span> 中国专利： CN114105744A </span> <span> . 2022-03-01</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061202511800.html">一种基于红外光谱与DFT计算的氨基酸吸附机制研究方法</a> <b>[P]</b> . <span> 中国专利： CN104749129B </span> <span> . 2017.07.21</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130405949300.html">2 METHOD FOR PRODUCING BICYCLIC COMPOUND VIA CLAISEN REARRANGEMENT</a> <b>[P]</b> . <span> 外国专利：  KR101816337B1 </span> <span> . 2018-01-08</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：2通过克莱森重排生产双环化合物的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130406695511.html">METHOD FOR PRODUCING BICYCLIC COMPOUND VIA CLAISEN REARRANGEMENT</a> <b>[P]</b> . <span> 外国专利：  HUE035366T2 </span> <span> . 2018-05-02</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：通过澄清重排生产双环化合物的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130406690356.html">Method for producing bicyclic compound via claisen rearrangement</a> <b>[P]</b> . <span> 外国专利：  IL229801A </span> <span> . 2017-11-30</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: 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