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绗叚绔� 鐐旂兇鍜屼簩鐑兇
鐐旂兇鐨勭祼(ji茅)妲�(g貌u)锛堢兎銆佺儻銆佺倲鐨勭祼(ji茅)妲�(g貌u)宸暟锛夛紝鍛藉悕鍜岀墿鐞嗘€ц唱(zh矛)锛涚倲鐑寸殑閰告€т互鍙婄倲鍖栫墿鐨勭敓
鎴愶紱鐐旂兇鐨勮Κ闆诲姞鎴愬弽鎳�(y墨ng)锛堝姞楣靛寲姘�銆侀沟绱�銆佹按锛�锛岃Κ鏍稿姞鎴愬弽鎳�(y墨ng)锛岀〖姘寲鍙嶆噳(y墨ng)锛屾哀鍖�锛屽姞
姘�锛岄倓鍘燂紝鑱氬悎绛夊叾瀹冨弽鎳�(y墨ng)锛岀儻鐑村拰鐐旂兇鍖栧(xu茅)鎬ц唱(zh矛)鐨勫皪(du矛)姣斿垎鏋�锛涚倲鐑寸殑閼掑垾鍜岀祼(ji茅)妲�(g貌u)娓�(c猫)瀹氾紙浣�
鐢ㄩ妧姘ㄦ憾娑�锛岄妳姘ㄦ憾娑诧紝楂橀尦閰搁墍婧舵恫锛岃嚟姘у寲-鍒嗚В鍙嶆噳(y墨ng)锛�锛涚倲鐑寸殑鍒跺倷锛堢敤閯颁簩楣典唬鐑�
鍜屽仌浜岄沟浠ｇ兎鍒跺倷鐐旂兇锛涢€氶亷(gu貌)鍋惰伅(li谩n)鍙嶆噳(y墨ng)鍒跺倷楂樼礆(j铆)鐐旂兇锛夛紝鍒濇浠嬬垂閫嗗悎鎴愬垎鏋�銆備簩鐑兇鐨勫垎
椤烇紙鍖呮嫭绱⿳浜岀儻鐑寸殑绔嬮珨鍖栧(xu茅)鍙婁笉绌�(w臎n)瀹氭€э級鑸囧懡鍚嶏紱鍏辫粵浜岀儻鐑寸殑绲�(ji茅)妲�(g貌u)锛岀儻涓欏熀纰虫闆㈠瓙銆�
鑷敱鍩哄強纰宠矤(f霉)闆㈠瓙鐨勭祼(ji茅)妲�(g貌u)锛堝叡杌涙晥鎳�(y墨ng)锛屽叡鎸珫锛岀啊(ji菐n)鍠粙绱逛紤鍏嬬埦鍒嗗瓙杌岄亾鐞嗚珫锛夛紱鍏辫粵浜岀儻
鐑寸殑鐩存帴鍔犳垚鑸囧叡杌涘姞鎴愶紙鑸囬沟绱�銆侀沟鍖栨矮鍔犳垚锛夛紝鐩搁棞(gu膩n)姗�(j墨)鐞嗕互鍙婂奖闊垮洜绱狅紙鍒濇浠嬬垂鍕�(d貌ng)鍔�
瀛�(xu茅)鎺у埗鐢�(ch菐n)鐗╄垏鐔卞姏瀛�(xu茅)鎺у埗鐢�(ch菐n)鐗╋級锛孌iels-Aider 鍙嶆噳(y墨ng)锛坰-闋嗗紡/鍙嶅紡妲�(g貌u)璞�锛屽崁(q奴)鍩熼伕鎿囨€э紝绔嬮珨灏�
涓€鍙嶆噳(y墨ng)锛岀啊(ji菐n)鍠粙绱瑰収(n猫i)鍨嬬敘(ch菐n)鐗┿€佸鍨嬬敘(ch菐n)鐗╀互鍙婃绱�(j铆)杌岄亾浣滅敤锛�銆�
绗竷绔� 鑺崇兇
鑻殑绲�(ji茅)妲�(g貌u)鐗规€у強琛ㄧず鏂瑰紡(Kekul茅绛�)锛岃姵棣欐€�(H眉ckel 瑕�(gu墨)鍓�)锛涜嫰琛嶇敓鐗╃殑鐣版(g貌u)鑸囧懡鍚嶏紱
鑻殑瑕浕鍙栦唬鍙嶆噳(y墨ng)锛堢鍖栧弽鎳�(y墨ng)銆侀沟鍖栧弽鎳�(y墨ng)銆佺：鍖栧弽鎳�(y墨ng)銆丗riedel-Crafts 鍙嶆噳(y墨ng) 銆丟attermann-Koch
鍙嶆噳(y墨ng)銆佹隘鐢插熀鍖栧弽鎳�(y墨ng)锛夊強鐩搁棞(gu膩n)姗�(j墨)鐞嗭紝鍙嶆噳(y墨ng)鍕�(sh矛)鑳藉湒锛涜嫰鐠�(hu谩n)涓婅Κ闆诲彇浠ｅ弽鎳�(y墨ng)鐨勫畾浣嶆晥鎳�(y墨ng)瑕�(gu墨)寰嬪拰瑙�
閲嬶紝澶氬厓鍙栦唬鑻殑瑕浕鍙栦唬缍�(j墨ng)椹�(y脿n)瑕�(gu墨)寰�锛涘鐠�(hu谩n)鑺崇兇鐨勫悎鎴�(Haworth 鍚堟垚娉�)锛涚兎鍩鸿嫰鍋�(c猫)閺堢殑鍙�
鎳�(y墨ng)锛堥沟鍖栧拰姘у寲锛�锛涘鑻唬鑴傜兇銆佽伅(li谩n)鑻鍖栧悎鐗╁拰绋犵挵(hu谩n)鑺崇兇锛堣悩銆佽捊銆佽彶锛夌殑绲�(ji茅)妲�(g貌u)鍙婂懡鍚�锛�
鑺抽鐑寸殑鍔犳垚鍙嶆噳(y墨ng)銆侀倓鍘熷弽鎳�(y墨ng)(Birch 閭勫師)鍜屾哀鍖栧弽鎳�(y墨ng)锛涢潪鑻姵棣欓珨绯汇€備簡瑙� H眉ckel 瑕�(gu墨)鍓囩殑
瑙ｉ噵锛堝垎瀛愯粚閬撶悊璜栵級鍜岃姵鐑寸殑渚�(l谩i)婧�銆�
绗叓绔� 楣典唬鐑村拰鏈夋(j墨)閲戝爆鍖栧悎鐗�
楣典唬鐑寸殑鍒嗛锛堣剛鑲棌楣典唬鐑�銆佽姵棣欓沟浠ｇ兇锛涢＝鍜岄沟浠ｇ兇銆佷笉椋藉拰楣典唬鐑�锛涗竴绱�(j铆)銆佷簩绱�(j铆)
鍜屼笁绱�(j铆)楣典唬鐑达紱涔欑儻鍨嬮沟浠ｇ兇銆佽嫰鍨嬮沟浠ｇ兇銆佺儻涓欏瀷楣典唬鐑�銆佽嫰鐢插瀷楣典唬鐑达紱鍋曚簩楣典唬鐑�銆�
閯颁簩楣典唬鐑�銆侀沟浠匡級鍙婂叾绲�(ji茅)妲�(g貌u)鐗归粸(di菐n)锛堝寘鎷彲妤靛寲鎬э級锛涢沟浠ｇ兇鐨勫懡鍚�锛涜Κ鏍稿彇浠ｅ弽鎳�(y墨ng)锛堝畾缇�锛�
搴曠墿銆佷腑蹇冪⒊鍘熷瓙銆佽Κ鏍歌│鍔戙€侀洟鍘诲熀鍦�(tu谩n)锛変互鍙� S 1銆丼 2 鍙嶆噳(y墨ng)姗�(j墨)鐞嗭紙瀹氱京銆佹(j墨)鐞�銆佺珛楂斿寲
N
N
瀛�(xu茅)銆佺壒榛�(di菐n)鍙婃噳(y墨ng)鐢�锛涘奖闊垮洜绱狅細鐑村熀绲�(ji茅)妲�(g貌u)锛岄洟鍘诲熀鍦�(tu谩n)锛岃│鍔戣Κ鏍告€у拰鍙嶆噳(y墨ng)姊濅欢锛涢劙鍩哄弮鑸囷級锛�
娑堝幓鍙嶆噳(y墨ng)鍙婂叾姗�(j墨)鐞嗭紙E1銆丒2 鍜� E1cb锛屽崁(q奴)鍩熼伕鎿囨€�銆佺珛楂旈伕鎿囨€�銆侀噸鎺掑弽鎳�(y墨ng)銆佹墡渚濆垏澶(gu墨)鍓�銆�
鎵庝緷鍒囧か鐢�(ch菐n)鐗┿€侀爢寮忔秷闄�銆佸弽寮忔秷闄わ級锛汼 1銆丼 2銆丒1銆丒2 鍥涚ó鍙嶆噳(y墨ng)姗�(j墨)鐞嗘瘮杓冿紱楣典唬鐑寸殑
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N
閭勫師鍙嶆噳(y墨ng)锛涢沟浠ｇ兇鐨勯憭鍒ワ紙鐢� AgNO 婧舵恫閼掑垾 1掳銆�2掳銆�3掳RX锛岄憭鍒� RI銆丷Br銆丷Cl锛夛紱楣�
3
浠ｇ兇鍦ㄦ湁姗�(j墨)鍚堟垚涓殑鎳�(y墨ng)鐢紙缍�(j墨ng)瑕牳鍙栦唬鍙嶆噳(y墨ng)鍒跺倷鍏跺畠楣典唬鐑�銆佺倲銆侀唶銆侀啔銆佽厛銆侀叝銆佽兒鎴栭姩
楣�锛岀鍩哄寲鍚堢墿銆佺枈姘寲鍚堢墿绛�锛涚稉(j墨ng)娑堥櫎鍙嶆噳(y墨ng)鍒跺倷鐑拰鐐�锛涚稉(j墨ng)閭勫師鐢熸垚鐑达級锛涢沟浠ｇ兇鐨勫埗鍌�
鏂规硶銆傛湁姗�(j墨)閲戝爆鍖栧悎鐗╁懡鍚�銆佺祼(ji茅)妲�(g貌u)鐗归粸(di菐n)锛涙湁姗�(j墨)閹傦紙Grignard 瑭﹀姂锛�锛屾湁姗�(j墨)閶�锛屾湁姗�(j墨)閵呯殑鍒跺倷
鍜屾噳(y墨ng)鐢紙鍋惰伅(li谩n)鍙嶆噳(y墨ng)锛�锛涢沟浠ｈ姵鐑寸殑瑕牳鍙栦唬锛堥噸榛�(di菐n)鏄秷鍘烩€斿姞鎴愭(j墨)鐞�锛屽嵆鑻倲姗�(j墨)鐞嗭級浠ュ強鎳�(y墨ng)
鐢�銆�
绗節绔� 娉㈣瓬瀛�(xu茅)鍩虹(ch菙)
绨�(ji菐n)鍠粙绱圭传澶栧厜璀�銆佺磪澶栧厜璀溿€佹牳纾佸叡鎸強璩�(zh矛)璀滅殑鍩烘湰鍘熺悊鍙婄敤浜庣⒑瀹氱啊(ji菐n)鍠湁姗�(j墨)鍖栧悎鐗�
绲�(ji茅)妲�(g貌u)鐨勬柟娉�銆傜传澶栧厜璀滐細鍩烘湰鍘熺悊鍜屾湁闂�(gu膩n)姒傚康(闆诲瓙韬嶉伔銆佺敓鑹插熀銆佸姪鑹插熀銆佸鑹叉晥鎳�(y墨ng)銆佹笡

  
 
鑹叉晥鎳�(y墨ng)銆佽棈(l谩n)绉诲拰绱呯Щ绛�)锛涚传澶栧厜璀滃湒锛浳籱ax 鑸囧寲瀛�(xu茅)绲�(ji茅)妲�(g貌u)鐨勯棞(gu膩n)绯伙紙Woodward-Fieser 瑕�(gu墨)寰嬶級銆�
绱呭鍏夎瓬锛氬熀鏈師鐞嗗拰鏈夐棞(gu膩n)姒傚康(鍖栧(xu茅)閸电殑浼哥府鎸嫊(d貌ng)銆佽畩褰㈡尟鍕�(d貌ng)绛�)锛涚磪澶栧厜璀滃湒锛堝惛鍏夊害銆�
閫忓皠姣�銆佸畼鑳藉湗(tu谩n)鍗€(q奴)銆佹寚绱嬪崁(q奴)锛�锛涘奖闊垮寲瀛�(xu茅)閸靛拰鍩哄湗(tu谩n)鐗瑰緛鍚告敹闋荤巼鐨勫洜绱�锛涢噸瑕佸畼鑳藉湗(tu谩n)鐨勭磪澶�
鐗瑰緛鍚告敹宄扮殑浣嶇疆锛涘湒璀滆В鏋愩€傛牳纾佸叡鎸細鍩烘湰鍘熺悊鍜屾湁闂�(gu膩n)姒傚康(璩�(zh矛)瀛愭牳纾佸叡鎸�銆�13C 鏍哥鍏�
鎸€佸睆钄芥晥鎳�(y墨ng)銆佸悇鍚戠暟鎬ф晥鎳�(y墨ng)銆佸寲瀛�(xu茅)浣嶇Щ銆佸伓鍚�銆佸寲瀛�(xu茅)绛夊児(ji脿))锛涘寲瀛�(xu茅)浣嶇Щ浠ュ強褰遍熆鍖栧(xu茅)浣嶇Щ
鐨勫洜绱�锛涚壒寰佽唱(zh矛)瀛愮殑鍖栧(xu茅)浣嶇Щ锛涜嚜鏃嬪伓鍚堣鍒嗚(gu墨)寰嬶紙n+1 瑕�(gu墨)寰嬶級锛涘湒璀滆В鏋�銆傝唱(zh矛)璀滐細鍩烘湰鍘�
鐞嗗拰鏈夐棞(gu膩n)姒傚康(鍒嗗瓙闆㈠瓙銆佸垎瀛愰洟瀛愬嘲銆佸悓浣嶇礌闆㈠瓙銆佸闆昏嵎闆㈠瓙銆佺鐗囬洟瀛�銆佷簽绌�(w臎n)闆㈠瓙锛�
楹ュ厠鎷夊か姊噸鎺�锛涚浉灏�(du矛)璞愬害)锛涜瑙ｈ(gu墨)寰�銆�
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閱囩殑绲�(ji茅)妲�(g貌u)锛堝寘鎷皪(du矛)鐗╃悊鎬ц唱(zh矛)銆佸寲瀛�(xu茅)鎬ц唱(zh矛)鐨勫奖闊匡級锛屽懡鍚�锛岀墿鐞嗘€ц唱(zh矛)鍜屽厜璀滅壒寰侊紱閱囩殑閰�
鍫挎€э紙闆诲瓙鏁堟噳(y墨ng)鍜岀┖闁撴晥鎳�(y墨ng)鐨勫奖闊匡級锛岄唶缇ュ熀涓矮鐨勫弽鎳�(y墨ng)锛岀兎姘у熀璨�(f霉)闆㈠瓙鐨勫牽鎬э紱閱囧拰鐒�(w煤)姗�(j墨)
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锛堢敤鏍兼皬瑭﹀姂銆佹湁姗�(j墨)閶拌│鍔戣垏鐠�(hu谩n)姘у寲鍚堢墿鎴栫景鍩哄寲鍚堢墿鍙嶆噳(y墨ng)锛岀倲閱囩殑鍚堟垚锛岄啗閰�銆佺晶閰稿強鍏�
琛嶇敓鐗╅倓鍘燂紝鐑兇姘村悎锛岀儻鐑寸櫦(f膩)鐢熺茎姹炲寲-鑴睘鍙嶆噳(y墨ng)锛�锛岄€嗗悎鎴愭硶绨�(ji菐n)浠嬨€傞啔鐨勭祼(ji茅)妲�(g貌u)锛堝寘鎷皪(du矛)
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绗崄浜岀珷 閱涘拰閰�
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Tiffeneau- Demjanov 閲嶆帓锛汣ope 娑堝幓锛涘閵ㄩ菇鍜屽閵ㄥ牽锛欻ofmann 娑堥櫎浠ュ強 E1cb 姗�(j墨)鐞�锛�
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