{"id":483,"date":"2023-12-25T16:30:39","date_gmt":"2023-12-25T08:30:39","guid":{"rendered":"https:\/\/www.yearnintl.com\/?p=483"},"modified":"2024-02-02T16:07:17","modified_gmt":"2024-02-02T08:07:17","slug":"dmso-oxidizer","status":"publish","type":"post","link":"https:\/\/www.yearnintl.com\/ko\/problems\/dmso-oxidizer\/","title":{"rendered":"DMSO \uc0b0\ud654\uc81c"},"content":{"rendered":"<p>\uc7a0\uc2dc \uc8fc\uae30\ud658 \ubc18\uc751\uc5d0\uc11c \uc2dc\uc120\uc744 \ub5bc\uace0 \ud070 \ucc45\uc5d0 \uc5b8\uae09\ub41c \ubc18\uc751 \uc911 \ud558\ub098\uc5d0 \ub300\ud574 \ub17c\uc758\ud574 \ubcf4\uaca0\uc2b5\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/1.jpg\" alt=\"DMSO oxidizer\" width=\"704\" height=\"203\" \/><\/p>\n<p>\ub354 \ud070 \ucc45\uc758 808\ud398\uc774\uc9c0\uc5d0 \ub098\uc624\ub294 \uc774 \ubc18\uc751\uc740 \uc54c\uce78 \ud560\ub77c\uc774\ub4dc\ub97c \uce74\ub974\ubcf4\ub2d0 \ud654\ud569\ubb3c\ub85c \uc0b0\ud654\uc2dc\ud0a4\ub294 DMSO\uc640 \ud615\uc2dd\uc801\uc73c\ub85c \ub3d9\ub4f1\ud55c Kornblum \ubc18\uc751\uc758 \uc608\uc785\ub2c8\ub2e4. \ubc18\uc751 \uba54\ucee4\ub2c8\uc998\uc740 Swern\uacfc \ub9e4\uc6b0 \uc720\uc0ac\ud569\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/2.jpg\" alt=\"DMSO oxidizer\" width=\"723\" height=\"241\" \/><\/p>\n<p>\ubcf4\uc2dc\ub2e4\uc2dc\ud53c, \uae30\uc9c8\uc758 C-H\uac00 \ud65c\uc131\ud654\ub418\uace0, \ubc18\uc751 \uc911\uc5d0 \ud615\uc131\ub41c \uc624\ub284 \uc774\uc628\uc5d0 \uc758\ud574 \uc2dc\uadf8\ub9c8 \uacb0\ud569 \uc804\uc790\uac00 \"\ub2f9\uaca8\uc838\" \ub098\uac00\uace0, \ub9c8\uc9c0\ub9c9\uc73c\ub85c \uc624\ub284 \uc774\uc628\uc740 \ud55c \uc30d\uc758 \uc804\uc790\ub97c \uc5bb\uc5b4 \ud669\ud654\ub514\uba54\ud2f8\ub85c \ud658\uc6d0\ub429\ub2c8\ub2e4. \uae30\uc9c8 \ud560\ub860\uc758 R\uc740 \uce74\ub974\ubcf4\ub2d0\uae30, \uc5d0\uc2a4\ud14c\ub974, \uce74\ub974\ubcf5\uc2e4\uc0b0 \ub610\ub294 \uc804\uc790 \ud761\uc778\uae30\uc5d0 \uc758\ud574 \ud65c\uc131\ud654\ub41c \ubc29\ud5a5\uc871\uc77c \uc218 \uc788\uace0, \ud560\ub85c\uac90 \uc6d0\uc790\ub294 Cl, Br, I\uc77c \uc218 \uc788\uc2b5\ub2c8\ub2e4. \ucd5c\uc801\ud654\ub41c \uc870\uac74\uc5d0\uc11c \uae30\uc9c8\uc740 \ub610\ud55c \uc9c0\ubc29\uc871 \ud560\ub85c\uac90\ud654\ubb3c\ub85c \ud655\uc7a5:<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/3.jpg\" alt=\"DMSO oxidizer\" width=\"689\" height=\"335\" \/><\/p>\n<p>\uc740 \uc774\uc628\uc744 \ucca8\uac00\ud558\uba74 \uae30\ud310\uc758 \ud560\ub85c\uac90 \uc6d0\uc790\uac00 \ud560\ub85c\uac90\ud654\uc740 \uce68\uc804\uc758 \ud615\ud0dc\ub85c \uc2dc\uc2a4\ud15c\uc744 \ub5a0\ub098\uac8c \ub418\uc5b4 DMSO\uc758 \uce5c\ud575\uc131 \uc0b0\uc18c \uc6d0\uc790\uc5d0 \ub354 \uc27d\uac8c \uacb0\ud569\ud560 \uc218 \uc788\ub294 \ud0c4\uc18c \uc591\uc131 \uc911\uc2ec\uc774 \uc0dd\uc131\ub429\ub2c8\ub2e4. \uc5ec\uae30\uc11c \ud2b8\ub9ac\uc5d0\ud2f8\uc544\ubbfc\uacfc \uac19\uc740 \ub354 \uac15\ud55c \uc5fc\uae30\ub97c \uc0ac\uc6a9\ud558\uc5ec \ud65c\uc131 \uc218\uc18c\ub97c \uc81c\uac70\ud560 \uc218 \uc788\uc2b5\ub2c8\ub2e4. \uc5ec\uae30\uc11c C-H\ub294 \uae30\uc9c8\uc774 \uc9c0\ubc29\uc871 \ud560\ub85c\uac90\ud654\ubb3c\uc774\uae30 \ub54c\ubb38\uc5d0 \ub35c \ud65c\uc131\uc774\uc9c0\ub9cc Swern\ucc98\ub7fc \ud2f0\uc624\uc77c\ub77c\uc774\ub4dc\ub97c \ud615\uc131\ud560 \uac00\ub2a5\uc131\uc774 \ub354 \ub192\uc73c\uba70 \uc774\ub3d9[2,3]\uc774 \ubc1c\uc0dd\ud569\ub2c8\ub2e4. \ud2f0\uc624\uc5d0\ud14c\ub974\ub97c \uc81c\uac70\ud558\ub824\uba74:<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/4.jpg\" alt=\"DMSO oxidizer\" width=\"724\" height=\"288\" \/><\/p>\n<p>\uc774\ub7ec\ud55c \uc870\uac74\uc5d0\uc11c \ubc18\uc751\uc774 \uc77c\uc5b4\ub098\ub824\uba74 \uc0c1\ub2f9\ud788 \ub192\uc740 \uc628\ub3c4\ub85c \uac00\uc5f4\ub418\uc5b4\uc57c \ud569\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/5.jpg\" alt=\"DMSO oxidizer\" width=\"701\" height=\"245\" \/><\/p>\n<p>\uc774\ub7ec\ud55c \uc870\uac74\uc5d0\uc11c \ubc18\uc751\uc774 \uc77c\uc5b4\ub098\ub824\uba74 \uc0c1\ub2f9\ud788 \ub192\uc740 \uc628\ub3c4\ub85c \uac00\uc5f4\ub418\uc5b4\uc57c \ud569\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/6.jpg\" alt=\"DMSO oxidizer\" width=\"714\" height=\"210\" \/><\/p>\n<p>\uc774\uc81c DMSO \ub300\uc2e0 \uc544\ubbfc\uc73c\ub85c \uc54c\ub9b4 \ud560\ub77c\uc774\ub4dc\ub97c \uc0b0\ud654\uc2dc\ucf1c \ubd88\ud3ec\ud654 \uce74\ub974\ubcf4\ub2d0 \ud654\ud569\ubb3c\uc744 \uc81c\uc870\ud558\ub294 \uac83\uc774 \ub354 \uc720\uc6a9\ud569\ub2c8\ub2e4. \uc774\ub294 \uc804\ud1b5\uc801\uc778 Kornblum \ubc18\uc751 \uc870\uac74\uc5d0\uc11c \uc218\ud589\ud560 \uacbd\uc6b0 \uae30\uc9c8\uc774 \ud30c\uad34\ub420 \uc218 \uc788\ub294 \ub9e4\uc6b0 \ub192\uc740 \uc628\ub3c4\ub85c \uac00\uc5f4\ud574\uc57c \ud569\ub2c8\ub2e4.<\/p>\n<p>DMSO\uc758 \uc0b0\ud654 \uc6a9\ub7c9\uc774 \uc5b4\ub514\uc5d0\uc11c \ub098\uc624\ub294\uc9c0 \ub2e4\uc2dc \uc0b4\ud3b4\ubcf4\uaca0\uc2b5\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/7.jpg\" alt=\"DMSO oxidizer\" width=\"682\" height=\"328\" \/><\/p>\n<p>DMSO \uc790\uccb4\ub294 \uacf5\uba85\uc744 \uac00\uc9c0\uba70 \ubc18\uc751 \uc2dc\uc2a4\ud15c\uc5d0\uc11c \ud3c9\ud615 \ud615\ud0dc\ub85c \uc874\uc7ac\ud558\uba70 \uc0b0\uc18c\ub294 \ud2b9\uc815 \uce5c\ud575\uc131 \ub2a5\ub825\uc744 \uac00\uc9c0\uba70 \ub8e8\uc774\uc2a4\uc0b0\uacfc \uacb0\ud569\ud560 \uc218 \uc788\uc2b5\ub2c8\ub2e4. \uadf8\ub7f0 \ub2e4\uc74c \ud669 \uc6d0\uc790\ub294 \ud560\ub85c\uac90\ud654\ubb3c \uc774\uc628\uacfc \uac19\uc740 \uc57d\ud55c \uce5c\ud575\uccb4\uc758 \uacf5\uaca9\uc744 \ubc1b\uc544 \uc0b0\ud654 \ub2a5\ub825\uc774 \uc788\ub294 \uc124\ud3ec\ub284 \uc774\uc628\uc744 \ud615\uc131\ud569\ub2c8\ub2e4. \uc5ec\uae30\uc11c \ub8e8\uc774\uc2a4\uc0b0\uc740 TFAA \ub610\ub294 \uc625\uc0b4\ub85c\uc77c \ud074\ub85c\ub77c\uc774\ub4dc\uc77c \uc218 \uc788\uc2b5\ub2c8\ub2e4. \ub8e8\uc774\uc2a4\uc0b0 \ubc18\uc751\uc5d0 TFAA\ub97c \uc0ac\uc6a9\ud558\ub294 \uacbd\uc6b0 \uc628\ub3c4\ub294 \uc77c\ubc18\uc801\uc73c\ub85c \uc57d -30\u00b0C\uc774\uace0, TFAA \ub300\uc2e0 \uc625\uc0b4\ub85c\uc77c \ud074\ub85c\ub77c\uc774\ub4dc\ub97c \uc0ac\uc6a9\ud558\ub294 \uacbd\uc6b0 \uc628\ub3c4\ub97c -78\u00b0C\ub85c \ub0ae\ucd94\uc5b4\uc57c \ud569\ub2c8\ub2e4. \ud53c\ub9ac\ub518\u00b7\uc0bc\uc0b0\ud654\ud669 \ubcf5\ud569\uccb4, DCC, \ubb34\uc218\ucd08\uc0b0, X2 \ub4f1\uc744 \uc0ac\uc6a9\ud55c\ub2e4\ub294 \ubcf4\uace0\ub3c4 \uc788\ub2e4. DCC \uc0ac\uc6a9 \ud6c4 \uc81c\ud488 \uc2dc\uc2a4\ud15c \ub0b4 \ubd80\uc0b0\ubb3c \uc694\uc18c\ub294 \ucc98\ub9ac\uac00 \uc5b4\ub835\ub2e4\ub294 \uc810\uc744 \uc5b8\uae09\ud560 \ub9cc\ud558\ub2e4. DCC\uac00 \ubc18\uc751\uc5d0 \ucc38\uc5ec\ud558\ub294 \ubc29\uc2dd\uc5d0 \uc775\uc219\ud558\uc9c0 \uc54a\uc740 \uacbd\uc6b0 Fukuyama \uce35 A007\uc744 \ucc38\uc870\ud560 \uc218 \uc788\uc2b5\ub2c8\ub2e4. \uc5ec\uae30\uc11c \ubc18\ubcf5\ud558\uc9c0 \ub9c8\uc2ed\uc2dc\uc624.<br \/>\uc720\uc0ac\ud55c \ubc18\uc751 \uba54\ucee4\ub2c8\uc998\uc744 \uae30\ubc18\uc73c\ub85c DMSO\ub294 \uc5d0\ud3ed\uc2dc\ub4dc \ubc0f \ubd88\ud3ec\ud654 \ud0c4\uc18c-\ud0c4\uc18c \uacb0\ud569\uacfc \uac19\uc740 \ud654\ud569\ubb3c\ub3c4 \uc0b0\ud654\ud560 \uc218 \uc788\uc2b5\ub2c8\ub2e4.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.yearnintl.com\/wp-content\/uploads\/2023\/12\/8.jpg\" alt=\"DMSO oxidizer\" width=\"586\" height=\"456\" \/><\/p>","protected":false},"excerpt":{"rendered":"<p>Let&#8217;s take our attention away from the pericyclic reaction for a moment and discuss one of the reactions mentioned in the big book: This reaction, which appears on page 808 of the larger book, is an example of the Kornblum reaction, which is formally equivalent to DMSO oxidizing an alkane halide to a carbonyl compound. The reaction mechanism is very similar to Swern: As you can see, the C-H of the substrate is activated, the sigma bond electrons are &#8220;pulled&#8221; away by the formed onium ion during the reaction, and finally the onium ion has gained a pair of electrons, which are reduced to dimethyl sulfide. The R in the substrate halon can be a carbonyl group, an ester, a carboxylic acid, or an aromatics activated by an electron-withdrawing group, and the halogen atom can be Cl, Br, I. Under optimized conditions, the substrate can also be extended to aliphatic\u2026<\/p>","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[26],"attr":[],"class_list":["post-483","post","type-post","status-publish","format-standard","hentry","category-problems","tag-dmso"],"_links":{"self":[{"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/posts\/483","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/comments?post=483"}],"version-history":[{"count":8,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/posts\/483\/revisions"}],"predecessor-version":[{"id":1234,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/posts\/483\/revisions\/1234"}],"wp:attachment":[{"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/media?parent=483"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/categories?post=483"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/tags?post=483"},{"taxonomy":"attr","embeddable":true,"href":"https:\/\/www.yearnintl.com\/ko\/wp-json\/wp\/v2\/attr?post=483"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}