{"id":17198,"date":"2017-12-21T06:17:26","date_gmt":"2017-12-20T22:17:26","guid":{"rendered":"\/\/www.gsbet888.com\/?p=17198"},"modified":"2019-08-02T18:52:12","modified_gmt":"2019-08-02T10:52:12","slug":"%e8%8b%af%e7%9a%84%e7%9b%b4%e6%8e%a5%e5%8d%95%e5%8f%96%e4%bb%a3%e7%83%b7%e5%9f%ba%e5%8c%96%e5%8f%8d%e5%ba%94","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/%e5%8c%96%e5%ad%a6%e6%9d%82%e8%ae%b0\/2017\/12\/%e8%8b%af%e7%9a%84%e7%9b%b4%e6%8e%a5%e5%8d%95%e5%8f%96%e4%bb%a3%e7%83%b7%e5%9f%ba%e5%8c%96%e5%8f%8d%e5%ba%94.html","title":{"rendered":"Science: \u82ef\u7684\u76f4\u63a5\u5355\u53d6\u4ee3\u70f7\u57fa\u5316\u53cd\u5e94"},"content":{"rendered":"<p>\u5728\u82ef\u73af\u4e0a\u5bfc\u5165\u70f7\u57fa\u7684\u65f6\u5019\uff0c\u5927\u5bb6\u4e00\u822c\u4f1a\u60f3\u5230\u7528\u4ec0\u4e48\u624b\u6cd5\uff1f<\/p>\n<h4><\/h4>\n<h4>\u82ef\u73af\u7684\u53d6\u4ee3\u53cd\u5e94<\/h4>\n<p>1877\u5e74\u4ee5\u6765\uff0c\u5728\u8fd9140\u5e74\u91cc\uff0c\u4e00\u76f4\u4f5c\u4e3a\u4ee3\u8868\u6027\u7684\u53cd\u5e94\u88ab\u4f7f\u7528\u7684\u662f\u3001<a href=\"\/\/www.gsbet888.com\/reactions\/2014\/03\/%e5%82%85-%e5%85%8b%e7%83%b7%e5%9f%ba%e5%8c%96%ef%bc%88friedel-crafts-alkylation%ef%bc%89.html\">Friedel-Craft\uff08FC\uff09\u53cd\u5e94<\/a>\u3002<sup>[1]\u3000<\/sup>FC\u53cd\u5e94\u4e2d\uff0c\u82ef\u73af\u4f5c\u4e3a\u4eb2\u6838\u5242\uff0c\u4e0e\u88ab\u8def\u6613\u65af\u9178\u6d3b\u5316\u540e\u7684\u5364\u4ee3\u70f7\u70c3\u53d1\u751f\u4eb2\u7535\u53d6\u4ee3\u53cd\u5e94\u53d1\u751f\u70f7\u57fa\u5316\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17200 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-0-1.jpg\" alt=\"\" width=\"419\" height=\"109\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-0-1.jpg 419w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-0-1-300x78.jpg 300w\" sizes=\"(max-width: 419px) 100vw, 419px\" \/><\/p>\n<p>\u800cFC\u53cd\u5e94\u7684\u7f3a\u70b9\u4e3b\u8981\u6709\u4ee5\u4e0b\u4e24\u70b9\u3001<br \/>\n\uff08\uff11\uff09\u53d6\u4ee3\u540e\u7684\u70f7\u57fa\u5316\u82ef\u73af\u7684\u4eb2\u6838\u6027\u6bd4\u539f\u6599\u82ef\u66f4\u9ad8\uff0c\u4f1a\u7ee7\u7eed\u53d1\u751f\u8fde\u9501\u70f7\u57fa\u5316\u53cd\u5e94\uff0c\u5f97\u5230\u591a\u53d6\u4ee3\u82ef\u3002<br \/>\n\uff08\uff12\uff09\u6d3b\u5316\u540e\u7684\u70f7\u57fa\u503e\u5411\u4e8e\u751f\u6210\u66f4\u7a33\u5b9a\u7684\u78b3\u9633\u79bb\u5b50\uff0c\u56e0\u6b64\u4e0d\u5bb9\u6613\u5f15\u5165\u76f4\u94fe\u578b\u7684\u70f7\u57fa\u3002<\/p>\n<p>\u4f5c\u4e3a\u4e0eFC\u53cd\u5e94\u76f8\u53cd\u7684\u65b9\u6cd5\u3001\u88ab\u79f0\u4e3a\u82b3\u9999\u65cf\u4eb2\u6838\u53d6\u4ee3\u53cd\u5e94\uff08SNAr\uff09\u3002\u8be5\u53cd\u5e94\uff0c\u9996\u5148\u662f\u4eb2\u6838\u5242\u4e0e\u82b3\u9999\u73af\u5e95\u7269\u53d1\u751f\u52a0\u6210\u53cd\u5e94\uff0c\u5f62\u6210\u03c3-complex\u4e2d\u95f4\u4f53\u3001\u7136\u540e\u518d\u53d1\u751fsp<sup>3<\/sup>\u78b3\u4e0a\u7684\u6d88\u9664\u53cd\u5e94\u5f97\u5230\u53d6\u4ee3\u82ef\u73af\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17201 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-00.jpg\" alt=\"\" width=\"434\" height=\"103\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-00.jpg 434w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-00-300x71.jpg 300w\" sizes=\"(max-width: 434px) 100vw, 434px\" \/><\/p>\n<p>\u987a\u4fbf\u8bf4\u4e00\u4e0b\uff0c\u4eb2\u6838\u8bd5\u5242\u662f\u6c27\u6216\u8005\u6c2e\u4eb2\u6838\u5242\u7684\u573a\u5408\u88ab\u79f0\u4e3aMeisenheimer\u6216\u8005Jackson-Meisenheimer complex\u3001\u800c\u78b3\u4eb2\u6838\u5242\u7684\u573a\u5408\u88ab\u79f0\u4e3aJanovsky complex\u3002<sup>[2]<\/sup><br \/>\n\u7531\u4e8e\u5e95\u7269\u662f6\u03c0\u5bcc\u7535\u5b50\u7684\u7a33\u5b9a\u82ef\u73af\uff0c\u6240\u4ee5\u5f88\u96be\u88ab\u4eb2\u6838\u8fdb\u653b\uff0c\u56e0\u6b64\u5fc5\u987b\u5148\u5728\u82ef\u73af\u4e0a\u5f15\u5165NO<sub>2<\/sub>\u57fa\u7b49\u5438\u7535\u5b50\u57fa\u56e2 (<strong>EWG<\/strong>)\u3002\u540c\u65f6\uff0c\u03c3-complex\u4e2d\u7684sp<sup>3<\/sup>\u78b3\u4e0a\u8fd8\u5f97\u6709\u5408\u9002\u7684\u79bb\u53bb\u57fa\u56e2\uff0c\u4f8b\u5982\uff0c\u5982\u679c\u662f\u96be\u79bb\u53bb\u7684\u6c22\u7684\u8bdd\uff0c\u8fd8\u5fc5\u987b\u6dfb\u52a0\u9002\u5f53\u7684\u6c27\u5316\u5242\u3002<sup>[3]<\/sup><\/p>\n<p>&nbsp;<\/p>\n<p>\u7136\u800c\u53ea\u662f\u7528\u65e0\u53d6\u4ee3\u82ef\u73af-\u82ef\u4f5c\u4e3a\u5e95\u7269\uff0c\u8fdb\u884c\u5355\u70f7\u57fa\u5316\u53cd\u5e94\u5c31\u65e0\u6cd5\u8fbe\u6210\u4e48\uff1f<\/p>\n<h4>\u9499Grignard\u8bd5\u5242<\/h4>\n<p><strong>Bath\u5927\u5b66\u7684<a href=\"http:\/\/www.bath.ac.uk\/chemistry\/contacts\/academics\/michael_hill\/\">Hill<\/a>\u4e0eToulouse\u5927\u5b66\u7684<a href=\"http:\/\/lpcno.insa-toulouse.fr\/spip.php?article422\">Maron<\/a>\u7b49\u4eba\u3001\u5236\u5907\u5206\u79bb\u51fa\u4e86\u9499\u7684\u70f7\u57fa\u683c\u5f0f\u8bd5\u5242\u7684\u7b49\u4ef7\u4f53\uff0c\u4f5c\u4e3a\u4eb2\u7535\u8bd5\u5242\u6210\u529f\u5b9e\u73b0\u4e86\u82ef(C<sub>6<\/sub>H<sub>6<\/sub>)\u7684\u76f4\u63a5\u5355\u53d6\u4ee3\u70f7\u57fa\u5316\u53cd\u5e94\u3002<\/strong><\/p>\n<blockquote><p>Andrew S. S. Wilson, Michael S. Hill, Mary F. Mahon, Chiara Dinoi, Laurent Maron<br \/>\n<em>Science<\/em> <strong>2017<\/strong>, <em>358<\/em>, 1168-1171. <a href=\"http:\/\/science.sciencemag.org\/content\/358\/6367\/1168\">doi:10.1126\/science.aao5923<\/a><\/p><\/blockquote>\n<p>\u6c22\u5316\u9499\u4e8c\u805a\u4f53<strong>\uff11<\/strong>\u3001\u53ef\u4ee5\u901a\u8fc7\u5355\u4f53\u9499\u9170\u80fa\u4e0ePhSiH<sub>3<\/sub>\u53cd\u5e94\u5236\u5907\u3001\u53cd\u5e94\u5f88\u7b80\u4fbf\uff0c\u5e76\u4e14\u53ef\u4ee5\u8fbe\u523070\uff05\u4ee5\u4e0a\u7684\u7eaf\u5316\u4ea7\u7387\u3002\u5728\u91cd\u82ef\u4e2d\uff0c\u5ba4\u6e29\u4e0b\u5316\u5408\u7269<strong>\uff11<\/strong>\u4e0e\u70ef\u70c3\u53cd\u5e94\uff0c\u4e5f\u5c31\u662fCa-H\u90e8\u4f4d\u4e0eC=C\u90e8\u4f4d\u53d1\u751f\u52a0\u6210\u751f\u6210\u76f4\u94fe\u72b6\u7684\u70f7\u57fa\u9499\u4ea7\u7269\u00a0<strong>2-4<\/strong>\u3002\uff38\u5c04\u7ebf\u5355\u6676\u884d\u5c04\u89e3\u6790\u8bc1\u5b9e\u3001\u751f\u6210\u7269\u00a0<strong>2<\/strong>\uff0c<strong>3<\/strong>\uff0c<strong>4<\/strong>\u4e3a\u4e8c\u805a\u4f53\u7ed3\u6784\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17202 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-1.jpg\" alt=\"\" width=\"678\" height=\"149\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-1.jpg 678w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-1-300x66.jpg 300w\" sizes=\"(max-width: 678px) 100vw, 678px\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17203 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-10.jpg\" alt=\"\" width=\"590\" height=\"222\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-10.jpg 768w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-10-300x113.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-10-680x256.jpg 680w\" sizes=\"(max-width: 590px) 100vw, 590px\" \/><\/p>\n<p style=\"text-align: center\"><em>\u56fe\u5f15\u7528\u81ea\u539f\u8457\u8bba\u6587<\/em><\/p>\n<p>\u5b9e\u9645\u4e0a\u572810\u5e74\u524d\uff0c\u4e5f\u5c31\u662f2007\u5e74\uff0c\u5316\u5408\u7269<strong>1<\/strong>\u4e2d\u7684Ca\u4e0a\u9644\u52a0\u6709THF\u5f62\u6210\u7684\u87af\u5408\u7269\u65e9\u5c31\u88abHarder\u7b49\u4eba\u62a5\u9053\u4e86\uff0c\u5e76\u4e14\u5df2\u7ecf\u8bc1\u660e\u8be5\u87af\u5408\u7269\u80fd\u591f\u4e0e\u82ef\u4e59\u70ef\u53cd\u5e94\u751f\u6210\u70f7\u57fa\u5316\u9499\u884d\u751f\u7269\u3002<sup>[4] <\/sup>\u4ed6\u4eec\u4e5f\u5f97\u5230\u4e86\u9488\u72b6\u7684\u8d64\u7ea2\u8272\u5316\u5408\u7269\u3002\u4f46\u662f\u5f88\u9057\u61be\u7684\u662f\uff0c\u5f53\u65f6\u4ed6\u4eec\u6ca1\u6709\u80fd\u591f\u6e05\u6670\u7684\u786e\u5b9a\u5176\u5206\u5b50\u7ed3\u6784\u3002\u800c\u65e9\u5728100\u5e74\u524d\uff0c\u9499\u7684\u683c\u5f0f\u8bd5\u5242\u7684\u5408\u6210\u65e9\u5c31\u5df2\u7ecf\u88ab\u5c1d\u8bd5\u5408\u6210<sup>[5]<\/sup>\u00a0\u5e76\u4e14\u5230\u4eca\u5e74\u4e3a\u6b62\uff0c\u5df2\u7ecf\u62a5\u9053\u4e86\u82b3\u57fa\uff0c\u82c4\u57fa\uff0c\u4e09\u7532\u57fa\u7532\u7845\u70f7\u57fa\u7532\u57fa\u53d6\u4ee3\u7684\u9499\u884d\u751f\u7269\u7684\u7ed3\u6784\uff0c\u800c\u8fd9\u4e00\u6b21\u662f\u7b2c\u4e00\u6b21\u62a5\u9053\u4e86\u76f4\u94fe\u578b\u7684\u70f7\u57fa\u53d6\u4ee3\u9499\u5316\u5408\u7269\u7684\u5408\u6210\u4e0e\u5206\u5b50\u7ed3\u6784\u7684\u89e3\u6790\u3002<\/p>\n<h4>\u82ef\u73af\u7684\u76f4\u63a5\u70f7\u57fa\u5316\u53cd\u5e94<\/h4>\n<p>\u4f5c\u8005\u7b49\u4eba\u5728\u4f18\u5316\u4e59\u57fa\u9499\u884d\u751f\u7269<strong>2<\/strong>\u7684\u5408\u6210\u6cd5\u8fc7\u7a0b\u4e2d\u53d1\u73b0C<sub>6<\/sub>D<sub>6<\/sub>\u6539\u6210d<sub>12<\/sub>-\u73af\u5df1\u70f7\uff0c\u5316\u5408\u7269<strong>2<\/strong>\u7684\u7a33\u5b9a\u6027\u5f97\u5230\u663e\u8457\u63d0\u9ad8\u3002\u800c\u5728\u4f7f\u7528C<sub>6<\/sub>D<sub>6<\/sub>\u4f5c\u4e3a\u6eb6\u5242\u7684\u65f6\u5019\uff0c\u53d1\u73b0\u751f\u6210\u4e86d<sub>5<\/sub>-\u4e59\u57fa\u53d6\u4ee3\u7684\u82ef\u73af\uff0c\u8fd9\u4e2a\u610f\u5916\u7684\u53d1\u73b0\u4e5f\u6210\u5c31\u4e86\u4eca\u5929\u8fd9\u4e00\u7bc7Science\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17204 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-2.jpg\" alt=\"\" width=\"560\" height=\"149\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-2.jpg 560w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-2-300x80.jpg 300w\" sizes=\"(max-width: 560px) 100vw, 560px\" \/><\/p>\n<p>&nbsp;<\/p>\n<h4>\u53cd\u5e94\u673a\u7406\u4e3aS<sub>N<\/sub>2\u578b<\/h4>\n<p>\u7406\u8bba\u8ba1\u7b97\u7684\u7ed3\u679c\u53d1\u73b0\uff0c\u53cd\u5e94\u5e76\u4e0d\u662f\u03c3\u952e\u590d\u5206\u89e3\uff0c\u800c\u662fS<sub>N<\/sub>2\u578b\u8fdb\u884c\u7684\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17205 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-3-1.jpg\" alt=\"\" width=\"834\" height=\"157\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-3-1.jpg 834w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-3-1-300x56.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-3-1-768x145.jpg 768w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-3-1-680x128.jpg 680w\" sizes=\"(max-width: 834px) 100vw, 834px\" \/>\u53e6\u5916\uff0c\u53cd\u5e94\u7684rate-detemination step\u662f\u53d1\u751f\u5728\u70f7\u57fa\u9499\u4e8c\u805a\u4f53\u8f6c\u53d8\u6210\u4e24\u4e2a\u5355\u4f53\u7684\u8fc7\u7a0b\uff0c\u800c\u4eb2\u6838\u53d6\u4ee3\u53cd\u5e94\u9636\u6bb5\u5e76\u6ca1\u6709\u591a\u5c11\u80fd\u91cf\u5c4f\u969c\uff0c\u8fd9\u4e2a\u53d1\u73b0\u5f88\u6709\u610f\u601d\u3002<\/p>\n<p style=\"text-align: center\">\uff08\u4e0b\u56fe\u5f15\u7528\u81ea\u539f\u8457\u8bba\u6587\uff09<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-17206 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-30.jpg\" alt=\"\" width=\"768\" height=\"518\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-30.jpg 768w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-30-300x202.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2017\/12\/rk12012018fig-30-680x459.jpg 680w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><\/p>\n<p>\u4e5f\u5c31\u662f\u8bf4\uff0c\u70f7\u57fa\u9499\u7684\u5355\u4f53\uff0c\u6d3b\u6027\u975e\u5e38\u5f3a\u3002\u8fd9\u4e2a\u4e8c\u805a\u4f53\u2192\u5355\u4f53\u7684\u8f6c\u6362\u662f\u672c\u53cd\u5e94\u8fbe\u6210\u7684\u5173\u952e\u3002\u540c\u65f6\u4ece\u8ba1\u7b97\u7ed3\u679c\u770b\u6765\uff0cCa\u53c2\u4e0e\u4e86\u62d4\u53bb\u82ef\u73af\u4e0a\u7684\u6c22\u7684\u8fc7\u7a0b\u3001\u800c\u5bf9\u6bd4\u4e0eHarder\u7b49\u4eba\u7684Ca(tfh)\u5316\u5408\u7269\uff0c\u672c\u8bba\u6587\u4e2d\u7684\u9499\u683c\u5f0f\u8bd5\u5242\u4e0a\u5e76\u6ca1\u6709\u914d\u4f4d\u6027\u6eb6\u5242\u7684\u9644\u7740\uff0c\u56e0\u6b64\u4e5f\u662f\u672c\u53cd\u5e94\u88ab\u53d1\u73b0\u7684\u4e00\u4e2a\u5173\u952e\u3002\u53d6\u4ee3\u53cd\u5e94\u540e\uff0c\u672c\u6765\u7684\u6c22\u5316\u9499\u5316\u5408\u7269<strong>1<\/strong>\u80fd\u591f\u5f97\u5230\u518d\u751f\uff0c\u50ac\u5316\u91cf\u7684\u82ef\u73af\u7684\u70f7\u57fa\u5316\u4e5f\u662f\u6709\u53ef\u80fd\u5b9e\u73b0\u7684\u3002<\/p>\n<h4>\u53c2\u8003\u6587\u732e<\/h4>\n<ol>\n<li>C. Friedel, J.-M. Crafts, <em>Compt. Rend.<\/em> <strong>1877<\/strong>, <em>84<\/em>, 1392.\u00a0(<a href=\"http:\/\/gallica.bnf.fr\/ark:\/12148\/bpt6k30410\/f1386.table\">link<\/a>)<\/li>\n<li>M. Makosza, <em>Chem. Soc. Rev<\/em>., <strong>2010<\/strong>, 39, 2855. <a href=\"http:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2010\/cs\/b822559c#!divAbstract\">doi:\u00a010.1039\/B822559C<\/a><\/li>\n<li>(a) I. S. Kovalev et al., <em>Russ. Chem. Rev.<\/em> <strong>2015<\/strong>,\u00a084, 1191. <a href=\"http:\/\/iopscience.iop.org\/article\/10.1070\/RCR4462\">doi: org\/10.1070\/RCR4462<\/a> (b)\u00a0O. N. Chupakhin, V. N. Charushin, <em>Tetrahedron Lett.<\/em><strong>2016<\/strong>, 57, 2665. <a href=\"http:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403916304580\">doi: org\/10.1016\/j.tetlet.2016.04.084<\/a><\/li>\n<li>J. Spielmann, S. Harder, <em>Chem. Eur. J.<\/em> <strong>2017<\/strong>, <em>13<\/em>, 8928. <a href=\"http:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chem.200701028\/abstract\">doi:10.1002\/chem.200701028<\/a><\/li>\n<li>(a) E. Beckmann, <em>Chem. Ber.<\/em> <strong>1905<\/strong>, <em>38<\/em>, 904. <a href=\"http:\/\/onlinelibrary.wiley.com\/wol1\/doi\/10.1002\/cber.190503801160\/abstract\">doi: 10.1002\/cber.190503801160<\/a> (b) H. Gilman, F. Schulze, <em>J. Am. Chem. Soc.<\/em> <strong>1926<\/strong>, <em>48<\/em>, 2463. <a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01420a038\">doi: 10.1021\/ja01420a038<\/a><\/li>\n<\/ol>\n<h4>\u5173\u8054\u4e66\u7c4d\uff08\u65e5\u4e9a\u4ef7\u683c\uff09<\/h4>\n<div class=\"amazonjs_item amazonjs_book\">\n<div class=\"amazonjs_image\"><a class=\"amazonjs_link\" title=\"Side Reactions in Organic Synthesis II: Aromatic Substitutions\" href=\"https:\/\/www.amazon.co.jp\/Side-Reactions-Organic-Synthesis-Substitutions\/dp\/3527337210?SubscriptionId=AKIAI6Q3RDQBU2J6P3JQ&amp;tag=chemstation-22&amp;linkCode=xm2&amp;camp=2025&amp;creative=165953&amp;creativeASIN=3527337210\" target=\"_blank\" rel=\"noopener\" data-role=\"amazonjs_product\" data-asin=\"3527337210\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/images-fe.ssl-images-amazon.com\/images\/I\/51QaMMrreoL._SL160_.jpg\" alt=\"Side Reactions in Organic Synthesis II: Aromatic Substitutions\" width=\"111\" height=\"160\" \/><\/a><\/div>\n<div 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\u306b\u8868\u793a\u3055\u308c\u3066\u3044\u308b\u4fa1\u683c\u304a\u3088\u3073\u767a\u9001\u53ef\u80fd\u6642\u671f\u306e\u60c5\u5831\u304c\u9069\u7528\u3055\u308c\u307e\u3059\u3002\"><b>\u4fa1\u683c<\/b>\uffe5 8,471(2017\/12\/15 08:34\u6642\u70b9)<\/li>\n<li><b>\u51fa\u7248\u65e5<\/b>2014\/11\/28<\/li>\n<li><b>\u5546\u54c1\u30e9\u30f3\u30ad\u30f3\u30b0<\/b>261,798\u4f4d<\/li>\n<li><b>\u30cf\u30fc\u30c9\u30ab\u30d0\u30fc<\/b>1284\u30da\u30fc\u30b8<\/li>\n<li><b>ISBN-10<\/b>1482206900<\/li>\n<li><b>ISBN-13<\/b>9781482206906<\/li>\n<li><b>\u51fa\u7248\u793e<\/b>CRC Press<\/li>\n<\/ul>\n<\/div>\n<p><a class=\"amazonjs_review\" title=\"Organic Chemistry: A Mechanistic Approach \u30ab\u30b9\u30bf\u30de\u30fc\u30ec\u30d3\u30e5\u30fc\" 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data-role=\"amazonjs_product\" data-asin=\"4061536834\">\u82b3\u9999\u65cf\u30d8\u30c6\u30ed\u74b0\u5316\u5408\u7269\u306e\u5316\u5b66-\u53cd\u5fdc\u6027\u3068\u74b0\u5408\u6210- (KS\u533b\u5b66\u30fb\u85ac\u5b66\u5c02\u9580\u66f8)<\/a><\/h4>\n<ul>\n<li><b>\u8457\u8005<\/b>\u5ee3\u8c37 \u529f,\u5742\u672c \u5c1a\u592b<\/li>\n<li class=\"amazonjs_price\" title=\"\u4fa1\u683c\u304a\u3088\u3073\u767a\u9001\u53ef\u80fd\u6642\u671f\u306f\u8868\u793a\u3055\u308c\u305f\u65e5\u4ed8\/\u6642\u523b\u306e\u6642\u70b9\u306e\u3082\u306e\u3067\u3042\u308a\u3001\u5909\u66f4\u3055\u308c\u308b\u5834\u5408\u304c\u3042\u308a\u307e\u3059\u3002\u5546\u54c1\u306e\u8ca9\u58f2\u306b\u304a\u3044\u3066\u306f\u3001\u8cfc\u5165\u306e\u6642\u70b9\u3067 [Amazon.co.jp \u307e\u305f\u306f Javari.jp] \u306b\u8868\u793a\u3055\u308c\u3066\u3044\u308b\u4fa1\u683c\u304a\u3088\u3073\u767a\u9001\u53ef\u80fd\u6642\u671f\u306e\u60c5\u5831\u304c\u9069\u7528\u3055\u308c\u307e\u3059\u3002\"><b>\u4fa1\u683c<\/b>\uffe5 20,496(2017\/12\/15 20:16\u6642\u70b9)<\/li>\n<li><b>\u51fa\u7248\u65e5<\/b>2008\/10\/30<\/li>\n<li><b>\u5546\u54c1\u30e9\u30f3\u30ad\u30f3\u30b0<\/b>1,192,753\u4f4d<\/li>\n<li><b>\u5358\u884c\u672c<\/b>222\u30da\u30fc\u30b8<\/li>\n<li><b>ISBN-10<\/b>4061536834<\/li>\n<li><b>ISBN-13<\/b>9784061536838<\/li>\n<li><b>\u51fa\u7248\u793e<\/b>\u8b1b\u8ac7\u793e<\/li>\n<\/ul>\n<\/div>\n<p><a class=\"amazonjs_review\" title=\"\u82b3\u9999\u65cf\u30d8\u30c6\u30ed\u74b0\u5316\u5408\u7269\u306e\u5316\u5b66-\u53cd\u5fdc\u6027\u3068\u74b0\u5408\u6210- (KS\u533b\u5b66\u30fb\u85ac\u5b66\u5c02\u9580\u66f8) \u30ab\u30b9\u30bf\u30de\u30fc\u30ec\u30d3\u30e5\u30fc\" href=\"https:\/\/www.amazon.jp\/reviews\/iframe?akid=AKIAI6Q3RDQBU2J6P3JQ&amp;alinkCode=xm2&amp;asin=4061536834&amp;atag=chemstation-22&amp;exp=2017-12-16T11%3A16%3A52Z&amp;v=2&amp;sig=wacMYMtBVvbu4A6zGKO9JUWuWimV6%252Bp5Qqx3oYRfe88%253D&amp;TB_iframe=true&amp;height=500&amp;width=600\" target=\"_blank\" rel=\"noopener\">\u30ab\u30b9\u30bf\u30de\u30fc\u30ec\u30d3\u30e5\u30fc\u3092\u898b\u308b<\/a><\/p>\n<div class=\"amazonjs_footer\"><\/div>\n<\/div>\n<h4>\u5173\u8054\u94fe\u63a5<\/h4>\n<ul>\n<li>Perspective: <a href=\"http:\/\/science.sciencemag.org\/content\/358\/6367\/1132\">Science<\/a><\/li>\n<li>\u82b3\u9999\u65cf\u4eb2\u6838\u53d6\u4ee3\u53cd\u5e94\uff1a<a href=\"https:\/\/ja.wikipedia.org\/wiki\/%E8%8A%B3%E9%A6%99%E6%97%8F%E6%B1%82%E6%A0%B8%E7%BD%AE%E6%8F%9B%E5%8F%8D%E5%BF%9C\">Wikipedia<\/a><\/li>\n<\/ul>\n<p>\u672c\u6587\u7248\u6743\u5c5e\u4e8e<strong>\u00a0<a href=\"\/\/www.gsbet888.com\/\">Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c<\/strong> \u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01 <\/p>\n","protected":false},"excerpt":{"rendered":"\u5728\u82ef\u73af\u4e0a\u5bfc\u5165\u70f7\u57fa\u7684\u65f6\u5019\uff0c\u5927\u5bb6\u4e00\u822c\u4f1a\u60f3\u5230\u7528\u4ec0\u4e48\u624b\u6cd5\uff1f \u82ef\u73af\u7684\u53d6\u4ee3\u53cd\u5e94 1877\u5e74\u4ee5\u6765\uff0c\u5728\u8fd9140\u5e74\u91cc\uff0c\u4e00\u76f4\u4f5c\u4e3a\u4ee3\u8868\u6027\u7684\u53cd\u5e94\u88ab\u4f7f\u7528\u7684\u662f\u3001Friedel-Craft\uff08FC\uff09\u53cd\u5e94\u3002[1]\u3000FC\u53cd\u5e94\u4e2d\uff0c\u82ef\u73af\u4f5c\u4e3a\u4eb2\u6838\u5242\uff0c\u4e0e\u88ab\u8def\u6613\u65af\u9178\u6d3b\u5316\u540e\u7684\u5364\u4ee3\u70f7\u70c3\u53d1\u751f\u4eb2\u7535\u53d6\u4ee3\u53cd\u5e94\u53d1\u751f\u70f7\u57fa\u5316\u3002 \u800cFC\u53cd\u5e94\u7684\u7f3a\u70b9\u4e3b\u8981\u6709\u4ee5\u4e0b\u4e24\u70b9\u3001 \uff08\uff11\uff09\u53d6\u4ee3\u540e\u7684\u70f7\u57fa\u5316\u82ef\u73af\u7684\u4eb2\u6838\u6027\u6bd4\u539f\u6599\u82ef\u66f4\u9ad8\uff0c\u4f1a\u7ee7\u7eed\u53d1\u751f\u8fde\u9501\u70f7\u57fa\u5316\u53cd\u5e94\uff0c\u5f97\u5230\u591a\u53d6\u4ee3\u82ef\u3002 \uff08\uff12\uff09\u6d3b\u5316\u540e\u7684\u70f7\u57fa\u503e\u5411\u4e8e\u751f\u6210\u66f4\u7a33\u5b9a\u7684\u78b3\u9633\u79bb\u5b50\uff0c\u56e0\u6b64\u4e0d\u5bb9\u6613\u5f15\u5165\u76f4\u94fe\u578b\u7684\u70f7\u57fa\u3002 \u4f5c\u4e3a\u4e0eFC\u53cd\u5e94\u76f8\u53cd\u7684\u65b9\u6cd5\u3001\u88ab\u79f0\u4e3a\u82b3\u9999\u65cf\u4eb2\u6838\u53d6\u4ee3\u53cd\u5e94\uff08SNAr\uff09\u3002\u8be5\u53cd\u5e94\uff0c\u9996\u5148\u662f\u4eb2\u6838\u5242\u4e0e\u82b3\u9999\u73af\u5e95\u7269\u53d1\u751f\u52a0\u6210\u53cd\u5e94\uff0c\u5f62\u6210\u03c3-complex\u4e2d\u95f4\u4f53\u3001\u7136\u540e\u518d\u53d1\u751fsp3\u78b3\u4e0a\u7684\u6d88\u9664\u53cd\u5e94\u5f97\u5230\u53d6\u4ee3\u82ef\u73af\u3002 \u987a\u4fbf\u8bf4\u4e00\u4e0b\uff0c\u4eb2\u6838\u8bd5\u5242\u662f\u6c27\u6216\u8005\u6c2e\u4eb2\u6838\u5242\u7684\u573a\u5408\u88ab\u79f0\u4e3aMeisenheimer\u6216\u8005Jackson-Meisenheimer complex\u3001\u800c\u78b3\u4eb2\u6838\u5242\u7684\u573a\u5408\u88ab\u79f0\u4e3aJanovsky complex\u3002[2] \u7531\u4e8e\u5e95\u7269\u662f6\u03c0\u5bcc\u7535\u5b50\u7684\u7a33\u5b9a\u82ef\u73af\uff0c\u6240\u4ee5\u5f88\u96be\u88ab\u4eb2\u6838\u8fdb\u653b\uff0c\u56e0\u6b64\u5fc5\u987b\u5148\u5728\u82ef\u73af\u4e0a\u5f15\u5165NO2\u57fa\u7b49\u5438\u7535\u5b50\u57fa\u56e2 (EWG)\u3002\u540c\u65f6\uff0c\u03c3-complex\u4e2d\u7684sp3\u78b3\u4e0a\u8fd8\u5f97\u6709\u5408\u9002\u7684\u79bb\u53bb\u57fa\u56e2\uff0c\u4f8b\u5982\uff0c\u5982\u679c\u662f\u96be\u79bb\u53bb\u7684\u6c22\u7684\u8bdd\uff0c\u8fd8\u5fc5\u987b\u6dfb\u52a0\u9002\u5f53\u7684\u6c27\u5316\u5242\u3002[3] &nbsp; \u7136\u800c\u53ea\u662f\u7528\u65e0\u53d6\u4ee3\u82ef\u73af-\u82ef\u4f5c\u4e3a\u5e95\u7269\uff0c\u8fdb\u884c\u5355\u70f7\u57fa\u5316\u53cd\u5e94\u5c31\u65e0\u6cd5\u8fbe\u6210\u4e48\uff1f \u9499Grignard\u8bd5\u5242 Bath\u5927\u5b66\u7684Hill\u4e0eToulouse\u5927\u5b66\u7684Maron\u7b49\u4eba\u3001\u5236\u5907\u5206\u79bb\u51fa\u4e86\u9499\u7684\u70f7\u57fa\u683c\u5f0f\u8bd5\u5242\u7684\u7b49\u4ef7\u4f53\uff0c\u4f5c\u4e3a\u4eb2\u7535\u8bd5\u5242\u6210\u529f\u5b9e\u73b0\u4e86\u82ef(C6H6)\u7684\u76f4\u63a5\u5355\u53d6\u4ee3\u70f7\u57fa\u5316\u53cd\u5e94\u3002 Andrew S. S. Wilson, Michael S. Hill, Mary F. Mahon, Chiara Dinoi, Laurent Maron Science 2017, 358, 1168-1171. doi:10.1126\/science.aao5923 \u6c22\u5316\u9499\u4e8c\u805a\u4f53\uff11\u3001\u53ef\u4ee5\u901a\u8fc7\u5355\u4f53\u9499\u9170\u80fa\u4e0ePhSiH3\u53cd\u5e94\u5236\u5907\u3001\u53cd\u5e94\u5f88\u7b80\u4fbf\uff0c\u5e76\u4e14\u53ef\u4ee5\u8fbe\u523070\uff05\u4ee5\u4e0a\u7684\u7eaf\u5316\u4ea7\u7387\u3002\u5728\u91cd\u82ef\u4e2d\uff0c\u5ba4\u6e29\u4e0b\u5316\u5408\u7269\uff11\u4e0e\u70ef\u70c3\u53cd\u5e94\uff0c\u4e5f\u5c31\u662fCa-H\u90e8\u4f4d\u4e0eC=C\u90e8\u4f4d\u53d1\u751f\u52a0\u6210\u751f\u6210\u76f4\u94fe\u72b6\u7684\u70f7\u57fa\u9499\u4ea7\u7269\u00a02-4\u3002\uff38\u5c04\u7ebf\u5355\u6676\u884d\u5c04\u89e3\u6790\u8bc1\u5b9e\u3001\u751f\u6210\u7269\u00a02\uff0c3\uff0c4\u4e3a\u4e8c\u805a\u4f53\u7ed3\u6784\u3002 \u56fe\u5f15\u7528\u81ea\u539f\u8457\u8bba\u6587 \u5b9e\u9645\u4e0a\u572810\u5e74\u524d\uff0c\u4e5f\u5c31\u662f2007\u5e74\uff0c\u5316\u5408\u72691\u4e2d\u7684Ca\u4e0a\u9644\u52a0\u6709THF\u5f62\u6210\u7684\u87af\u5408\u7269\u65e9\u5c31\u88abHarder\u7b49\u4eba\u62a5\u9053\u4e86\uff0c\u5e76\u4e14\u5df2\u7ecf\u8bc1\u660e\u8be5\u87af\u5408\u7269\u80fd\u591f\u4e0e\u82ef\u4e59\u70ef\u53cd\u5e94\u751f\u6210\u70f7\u57fa\u5316\u9499\u884d\u751f\u7269\u3002[4] \u4ed6\u4eec\u4e5f\u5f97\u5230\u4e86\u9488\u72b6\u7684\u8d64\u7ea2\u8272\u5316\u5408\u7269\u3002\u4f46\u662f\u5f88\u9057\u61be\u7684\u662f\uff0c\u5f53\u65f6\u4ed6\u4eec\u6ca1\u6709\u80fd\u591f\u6e05\u6670\u7684\u786e\u5b9a\u5176\u5206\u5b50\u7ed3\u6784\u3002\u800c\u65e9\u5728100\u5e74\u524d\uff0c\u9499\u7684\u683c\u5f0f\u8bd5\u5242\u7684\u5408\u6210\u65e9\u5c31\u5df2\u7ecf\u88ab\u5c1d\u8bd5\u5408\u6210[5]\u00a0\u5e76\u4e14\u5230\u4eca\u5e74\u4e3a\u6b62\uff0c\u5df2\u7ecf\u62a5\u9053\u4e86\u82b3\u57fa\uff0c\u82c4\u57fa\uff0c\u4e09\u7532\u57fa\u7532\u7845\u70f7\u57fa\u7532\u57fa\u53d6\u4ee3\u7684\u9499\u884d\u751f\u7269\u7684\u7ed3\u6784\uff0c\u800c\u8fd9\u4e00\u6b21\u662f\u7b2c\u4e00\u6b21\u62a5\u9053\u4e86\u76f4\u94fe\u578b\u7684\u70f7\u57fa\u53d6\u4ee3\u9499\u5316\u5408\u7269\u7684\u5408\u6210\u4e0e\u5206\u5b50\u7ed3\u6784\u7684\u89e3\u6790\u3002 \u82ef\u73af\u7684\u76f4\u63a5\u70f7\u57fa\u5316\u53cd\u5e94 \u4f5c\u8005\u7b49\u4eba\u5728\u4f18\u5316\u4e59\u57fa\u9499\u884d\u751f\u72692\u7684\u5408\u6210\u6cd5\u8fc7\u7a0b\u4e2d\u53d1\u73b0C6D6\u6539\u6210d12-\u73af\u5df1\u70f7\uff0c\u5316\u5408\u72692\u7684\u7a33\u5b9a\u6027\u5f97\u5230\u663e\u8457\u63d0\u9ad8\u3002\u800c\u5728\u4f7f\u7528C6D6\u4f5c\u4e3a\u6eb6\u5242\u7684\u65f6\u5019\uff0c\u53d1\u73b0\u751f\u6210\u4e86d5-\u4e59\u57fa\u53d6\u4ee3\u7684\u82ef\u73af\uff0c\u8fd9\u4e2a\u610f\u5916\u7684\u53d1\u73b0\u4e5f\u6210\u5c31\u4e86\u4eca\u5929\u8fd9\u4e00\u7bc7Science\u3002 &nbsp; \u53cd\u5e94\u673a\u7406\u4e3aSN2\u578b \u7406\u8bba\u8ba1\u7b97\u7684\u7ed3\u679c\u53d1\u73b0\uff0c\u53cd\u5e94\u5e76\u4e0d\u662f\u03c3\u952e\u590d\u5206\u89e3\uff0c\u800c\u662fSN2\u578b\u8fdb\u884c\u7684\u3002 \u53e6\u5916\uff0c\u53cd\u5e94\u7684rate-detemination step\u662f\u53d1\u751f\u5728\u70f7\u57fa\u9499\u4e8c\u805a\u4f53\u8f6c\u53d8\u6210\u4e24\u4e2a\u5355\u4f53\u7684\u8fc7\u7a0b\uff0c\u800c\u4eb2\u6838\u53d6\u4ee3\u53cd\u5e94\u9636\u6bb5\u5e76\u6ca1\u6709\u591a\u5c11\u80fd\u91cf\u5c4f\u969c\uff0c\u8fd9\u4e2a\u53d1\u73b0\u5f88\u6709\u610f\u601d\u3002 \uff08\u4e0b\u56fe\u5f15\u7528\u81ea\u539f\u8457\u8bba\u6587\uff09 \u4e5f\u5c31\u662f\u8bf4\uff0c\u70f7\u57fa\u9499\u7684\u5355\u4f53\uff0c\u6d3b\u6027\u975e\u5e38\u5f3a\u3002\u8fd9\u4e2a\u4e8c\u805a\u4f53\u2192\u5355\u4f53\u7684\u8f6c\u6362\u662f\u672c\u53cd\u5e94\u8fbe\u6210\u7684\u5173\u952e\u3002\u540c\u65f6\u4ece\u8ba1\u7b97\u7ed3\u679c\u770b\u6765\uff0cCa\u53c2\u4e0e\u4e86\u62d4\u53bb\u82ef\u73af\u4e0a\u7684\u6c22\u7684\u8fc7\u7a0b\u3001\u800c\u5bf9\u6bd4\u4e0eHarder\u7b49\u4eba\u7684Ca(tfh)\u5316\u5408\u7269\uff0c\u672c\u8bba\u6587\u4e2d\u7684\u9499\u683c\u5f0f\u8bd5\u5242\u4e0a\u5e76\u6ca1\u6709\u914d\u4f4d\u6027\u6eb6\u5242\u7684\u9644\u7740\uff0c\u56e0\u6b64\u4e5f\u662f\u672c\u53cd\u5e94\u88ab\u53d1\u73b0\u7684\u4e00\u4e2a\u5173\u952e\u3002\u53d6\u4ee3\u53cd\u5e94\u540e\uff0c\u672c\u6765\u7684\u6c22\u5316\u9499\u5316\u5408\u72691\u80fd\u591f\u5f97\u5230\u518d\u751f\uff0c\u50ac\u5316\u91cf\u7684\u82ef\u73af\u7684\u70f7\u57fa\u5316\u4e5f\u662f\u6709\u53ef\u80fd\u5b9e\u73b0\u7684\u3002 \u53c2\u8003\u6587\u732e C. Friedel, J.-M. Crafts, Compt. Rend. 1877, 84, 1392.\u00a0(link) M. Makosza, Chem. Soc. Rev., 2010, 39, 2855. doi:\u00a010.1039\/B822559C (a) I. S. Kovalev et al., Russ. Chem. Rev. 2015,\u00a084, 1191. doi: org\/10.1070\/RCR4462 (b)\u00a0O. N. Chupakhin, V. N. Charushin, Tetrahedron Lett.2016, 57, 2665. doi: org\/10.1016\/j.tetlet.2016.04.084 J. Spielmann, S. Harder, Chem. Eur. J. 2017, 13, 8928. doi:10.1002\/chem.200701028 (a) E. Beckmann, Chem. 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