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锛�1锛夌兎鐑寸殑楣靛寲鍙嶆噳(y墨ng)锛岀儻涓欏熀鍨�銆佺倲涓欏熀鍨嬬殑楣靛寲鍙嶆噳(y墨ng)锛岀景鍩�銆佺兎鍩鸿嫰
鐨勎�-楣靛寲鍙嶆噳(y墨ng)锛�
锛�2锛夎剛鐠�(hu谩n)鐑寸殑鍔犳矮锛屽姞楣电礌锛岄沟浠�锛屽姞楣靛寲姘�锛屾哀鍖�锛�
锛�3锛夐沟浠ｇ兇鐨勫彇浠ｅ弽鎳�(y墨ng)锛堝寘鎷秷闄ゅ弽鎳�(y墨ng)鍙� Saytzeff 瑕�(gu墨)鍓�锛岄倓鍘熷弽鎳�(y墨ng)锛屾牸
姘忓弽鎳�(y墨ng)锛屽叾浠栨湁姗�(j墨)閲戝爆鍖栧悎鐗╃殑鍙嶆噳(y墨ng)锛堝惈 Li锛孼n锛孋u 绛夛級锛�锛岀儻涓欏熀楣典唬鐑�銆�
鐐斾笝鍩洪沟浠ｇ兇銆佽姁鍩洪沟浠ｇ兇鑸囦箼鐑紡楣典唬鐑�銆侀沟浠ｈ嫰鐨勫弽鎳�(y墨ng)娲绘€ф瘮杓�锛�
锛�4锛夌儻鐑寸殑瑕浕鍔犳垚锛堥沟绱�锛岄沟鍖栨矮锛屾按锛岄唶锛屾楣甸吀锛夎垏 Markovnikov
瑕�(gu墨)寰嬶紝鑷敱鍩哄姞鎴愶紙婧村寲姘級鑸囧弽 Markovnikov 瑕�(gu墨)寰�锛岀〖姘寲鍙嶆噳(y墨ng)锛岃嚟姘у寲鍜�
KMnO4 姘у寲鍙婄珛楂旈伕鎿囨€э紝鍌寲鍔犳矮锛屽叡杌涗簩鐑兇鐨� 1,2-鍔犳垚锛堝嫊(d貌ng)鍔涘(xu茅)鎺у埗锛�
鑸� 1,4-鍔犳垚锛堝叡杌涘姞鎴�锛岀啽鍔涘(xu茅)鎺у埗锛夛紝Diels-Alder 鍙嶆噳(y墨ng)锛�
锛�5锛夌倲鐑寸殑鐐旀矮鍙嶆噳(y墨ng)锛屽姞鎴愬弽鎳�(y墨ng)锛堥沟绱狅紝楣靛寲姘�锛屾按锛夛紝纭兼矮鍖栧弽鎳�(y墨ng)锛岃嚟
姘у寲锛孠MnO4 姘у寲锛屽偓鍖栧姞姘紙H2/Lindlar 鍌寲鍔戯級锛岄倓鍘燂紙NH3/Na锛�锛岄沟浠ｈ姵
鐑寸殑姘磋В銆佽垏閲戝爆鐨勫弽鎳�(y墨ng)锛岃垏 NaNH2/NH3 鍙嶆噳(y墨ng)锛堣嫰鐐旂殑褰㈡垚鑸囨秷闄�-鍔犳垚鍙嶆噳(y墨ng)
姗�(j墨)鐞嗭級鍙婂崁(q奴)鍩熼伕鎿囨€�锛�
锛�6锛夊柈鐠�(hu谩n)銆佸鐠�(hu谩n)鑺崇兇鐨勮Κ闆诲彇浠ｅ弽鎳�(y墨ng) (楣典唬銆佺鍖�銆佺：鍖�銆丗riedel-crafts
鍙嶆噳(y墨ng)) 鍙婂畾浣嶈(gu墨)鍓�锛屾哀鍖栵紝鍌寲鍔犳矮锛孊irch 閭勫師锛�
锛�7锛夐唶鍜岄厷鐨勯吀鍫垮弽鎳�(y墨ng)锛岄唶鑸� HX 鐨勮Κ鏍稿彇浠ｅ弽鎳�(y墨ng)鑸囬噸鎺掔従(xi脿n)璞★紙楣靛寲姘�锛�
SOCl2锛孭X3 绛夛級锛岃劔姘磋垏閲嶆帓鐝�(xi脿n)璞�锛屾哀鍖�锛涢劙浜岄唶鐨� HIO4 姘у寲锛岄牷鍝唶閲嶆帓锛�
閰氱殑瑕浕鍙栦唬锛屾哀鍖�锛岀暟涓欒嫰姘у寲鍒跺倷鑻厷锛�
锛�8锛夎嫰鍩虹儻涓欏熀閱氬拰涔欑儻鍩虹儻涓欏熀閱氱殑 Claisen 閲嶆帓锛岄啔鐨� Williamson 鍚�
鎴愭硶鍜� Ullmann 鍚堟垚娉�锛岀挵(hu谩n)姘у寲鍚堢墿鐨勫埗娉曡垏闁嬬挵(hu谩n)鍙嶆噳(y墨ng)锛堝牽鎬ф浠惰垏閰告€ф浠�
鐨勬瘮杓冿級锛�
锛�9锛夐啗閰殑缇板熀鐨勮Κ鏍稿姞鎴愶紙HCN銆丯aHSO3銆丠2O銆丷OH銆丷MgX銆丯H3銆�
RNH2銆丠ONH2銆丠2NCONH2銆丠2NNHCONH2銆丳hNHNH2 绛夛級锛岄吀鍌寲伪-楣靛寲锛�
鍫垮偓鍖栁�-楣靛寲鑸囬沟浠垮弽鎳�(y墨ng)锛岀茎閱涚府鍚堝弽鎳�(y墨ng)锛岄倓鍘燂紙Clemmensen 閭勫師锛�
Wolff-Kishner-榛冮炒榫嶅弽鎳�(y墨ng)锛岄洐鍒嗗瓙閭勫師鑸囬劙浜岄唶鐨勭敓鎴愶級锛孋annizzaro 鍙嶆噳(y墨ng)锛�
姘у寲锛圚NO3锛孠MnO4锛孠2Cr2O7锛孴ollen 瑭﹀姂锛孲eO2锛�锛孏attermann-Koch 鍙嶆噳(y墨ng)
鍒跺倷鑺抽啗锛孒NO3 姘у寲瀹夋伅棣欒垏寮�(qi谩ng)鍫夸笅鐨勯噸鎺掑埗鍌欎簩鑻茎涔欓吀锛�
锛�10锛変笉椋藉拰閱涢叜鐨� 1,4-鍏辫粵鍔犳垚锛堣垏 HCN 鍙嶆噳(y墨ng)锛岃垏鐑唶璨�(f霉)闆㈠瓙鐨� Michael
鍙嶆噳(y墨ng)锛岃垏 R2CuLi 鐨勫弽鎳�(y墨ng)锛岃垏 RMgX/CuX 鐨勫弽鎳�(y墨ng)锛夊拰 1,2-鍔犳垚鍙嶆噳(y墨ng)锛圧Li锛�锛岄倓
鍘燂紝閱岀殑鍒跺倷鑸囧姞鎴愬弽鎳�(y墨ng)锛孋N-
鍌寲鐨勫畨鎭绺悎锛岄叜閱囩府鍚�锛岀儻閱囬菇鑸囬啗绺�
4
鍚堬紝Vilsmeier 鐢�?锛涱嚞纾�?y墨ng)鍒跺倷閰氶啗锛孯emier-Tiemann 鍙嶆噳(y墨ng)鍒跺倷閰氶啗锛孎(xi脿n)ries 閲�
鎺掑埗鍌欓厷閰�锛�
锛�11锛夌晶閰哥殑閰告€ц垏楣界殑褰㈡垚锛�?锛涱嚞纾�?y墨ng)锛堥叝鍖�锛岀敓鎴愰叞鑳�銆佽厛銆侀叞姘�銆�
閰愶級锛岃劔缇э紙Kolbe 鍙嶆噳(y墨ng)锛孒unsdiecker 鍙嶆噳(y墨ng)锛�锛屛�-H 楣典唬锛圚ell-Volhard-Zelinsky
鍙嶆噳(y墨ng)锛夛紝閭勫師锛屼簩鍏冪晶閰哥殑鐔卞垎瑙ｅ弽鎳�(y墨ng)锛�
锛�12锛夌晶閰歌鐢熺墿鐨勬按瑙ｅ弽鎳�(y墨ng)锛岄唶瑙�锛岄吀瑙ｏ紝姘ㄨВ锛岃垏鏈夋(j墨)閲戝爆鍖栧悎鐗╃殑
鍙嶆噳(y墨ng)锛岄叞姘殑 Rosenmund 閭勫師锛圚2锛孭d/BaSO4锛�锛岄叝鐨� Bouveault-Blanc 閭勫師锛�
Ritter 鍙嶆噳(y墨ng)锛岀儻閰殑鍒跺倷鑸囧弽鎳�(y墨ng)锛屽厜姘ｇ殑鍙嶆噳(y墨ng)锛岀⒊閰搁叝鐨勫弽鎳�(y墨ng)锛屽師閰搁叝鐨勫弽鎳�(y墨ng)锛�
閬庨吀鑸� Baeyer-Villiger 姘у寲锛�
锛�13锛塊noevenagel 绺悎鍙嶆噳(y墨ng)鑸囦笉椋藉拰缇ч吀鐨勫悎鎴�锛孭erkin 绺悎鍙嶆噳(y墨ng)鑸囦笉
椋藉拰缇ч吀鐨勫悎鎴愶紝Reformasky 鍙嶆噳(y墨ng)鑸囄�-閱囬吀閰殑鍚堟垚锛孠olbe-Schmidt 鍙嶆噳(y墨ng)鑸�
姘存閰哥殑鍚堟垚锛孋laisen 绺悎銆丏ieckmann 绺悎鑸囄�-閰吀閰殑鍚堟垚锛屼笝浜岄吀閰悎
鎴愭硶锛屼箼閰颁箼閰镐箼閰悎鎴愭硶锛孧ichael 鍙嶆噳(y墨ng)锛�
锛�14锛夎兒椤炵殑鐑村熀鍖�锛�?锛涱姮顕篶姘ㄥ熀鐨勪繚璀�(h霉)锛岃垏浜炵閰稿弽鎳�(y墨ng)锛屽彅鑳虹殑姘у寲
鑸� Cope 娑堥櫎鐢熸垚鐑兇锛岃姵鑳虹殑姘у寲銆佽Κ闆诲彇浠ｅ弽鎳�(y墨ng)锛岃兒鐨勫埗鍌欙紙Gabriel 鍚堟垚
娉�锛岄啗閰殑閭勫師鑳哄寲锛岀鍩哄寲鍚堢墿銆侀叞鑳�銆佽偀鍜岃厛鐨勯倓鍘�锛孒ofmann 閲嶆帓锛夛紝
鐑兒鐨勫埗鍌欒垏鍙嶆噳(y墨ng)锛孧ichael 鍙嶆噳(y墨ng)锛屽閵ㄥ牽鐨� Hofmann 鐔辨秷闄ょ敓鎴愮儻鐑�锛�
锛�15锛夌鍩鸿嫰琛嶇敓鐗╃殑 ArSN 鍙嶆噳(y墨ng)锛岀鍩虹敳鐑风殑閰告€ц垏 Henry 鍙嶆噳(y墨ng)锛岄噸姘敳鐑�
鐨勮Κ鏍告€ц垏鍙嶆噳(y墨ng)锛堢敳鍩哄寲鍙嶆噳(y墨ng)锛岃垏閱涢叜鐨勫弽鎳�(y墨ng)锛岃垏閰版隘鐨勫弽鎳�(y墨ng)鍙� Wolff 閲嶆帓鈥�
澧� 闀�(zh菐ng) 纰� 閺� 鐨� Arndt-Eistert 鍚� 鎴� 娉� 锛�锛� 鐑� 鐑� 鑸� CH2I2 鍦� Zn(Cu) 浣� 鐢� 涓� 鐨�
Simmons-Smith 鍙嶆噳(y墨ng)鍚堟垚鐠�(hu谩n)涓欑兎琛嶇敓鐗╋紝CHX3 鍦ㄥ挤(qi谩ng)鍫垮偓鍖栦笅鑸囩儻鐑寸殑鍙嶆噳(y墨ng)鍚�
鎴愪簩楣电挵(hu谩n)涓欑兎琛嶇敓鐗�锛岄噸姘菇鐨勫埗鍌欒垏绌�(w臎n)瀹氭€�锛岄噸姘菇鐨勫弽鎳�(y墨ng)锛堢啽鍒嗚В鎴愰厷鍜�
楣靛寲鐗�锛屾盁鑻殑鍒跺倷锛孲andmeyer 鍙嶆噳(y墨ng)鑸囪姵姘�銆佽姵婧�銆佽姵鑵堢殑鍒跺倷锛岄倓鍘熻劔姘�锛�
Gatterman 鍙嶆噳(y墨ng)鑸囪厛鍩鸿嫰琛嶇敓鐗╃殑鍒跺倷锛岄倓鍘熸垚鑲�锛屽伓鑱�(li谩n)鍙嶆噳(y墨ng)鑸囧伓姘寲鍚堢墿鐨�
鍚堟垚锛夛紝鍋舵爱鍖栧悎鐗╅倓鍘熻垏浜岃嫰鑲肩殑鑱�(li谩n)鑻兒閲嶆帓锛岀枈姘寲鍚堢墿鑸� Curtius 閲嶆帓銆�
Schmidt 閲嶆帓锛�
锛�16锛夌～閱囩殑閰告€ц垏鎴愰菇鍙嶆噳(y墨ng)锛岀～閱囩殑姘у寲锛岀～閱囪垏纭厷鐨勫埗鍌�锛岀～閱氱殑
鍒跺倷鑸囨哀鍖栧弽鎳�(y墨ng)锛岀：閰�銆佷簽纾洪吀鐨勫埗鍌欒垏鍙嶆噳(y墨ng)锛岀～閰镐簩鐢查叝鐨勫弽鎳�(y墨ng)锛屼笁鐑峰熀鑶�
鐨勫弽鎳�(y墨ng)锛學ittig 鍙嶆噳(y墨ng)銆丠orner-Emmons 鍙嶆噳(y墨ng)锛屾隘鍖栦笁鐢插熀纭呬繚璀�(h霉)缇ュ熀鐨勬柟娉�锛�
锛�17锛夊悺鍜�銆佸憢鍠冦€佸櫥鍚╅洔鍘熷瓙涓婄殑鍙栦唬鍙嶆噳(y墨ng)銆佺⒊鍘熷瓙涓婄殑鍙栦唬鍙嶆噳(y墨ng)锛屼簲
鍏冮洔鐠�(hu谩n)鐨勫悎鎴愶紙Knorr 鍚堟垚娉曘€丠antzesch 鍚堟垚娉曠瓑锛�锛岀碃閱涚殑宸ユキ(y猫)鍒跺倷鏂规硶锛�
瑕浕鍙栦唬娲绘€ц垏瀹氫綅瑕�(gu墨)寰�锛屽悺鍟剁殑瑕浕鍙栦唬鑸囪Κ鏍稿彇浠ｏ紝Chichibabin 鍙嶆噳(y墨ng)鑸�
2-姘ㄥ熀鍚″暥鐨勫埗鍌�锛屽柟鍟夌殑 Skraup 鍚堟垚娉曘€丏?ebner-Miller 鍚堟垚娉�锛岀暟鍠瑰晧鐨�
Bischler-Napieralski 鍚堟垚娉曪紝鍠瑰晧鑸囩暟鍠瑰晧鐨勫彇浠ｅ弽鎳�(y墨ng)锛屽槯鍟跺拰鍢屽懁鐠�(hu谩n)鐨勫悎鎴愶紱
锛�18锛夐浕鐠�(hu谩n)鍖栧弽鎳�(y墨ng)鑸囬伕鎿囨€ц(gu墨)寰�锛岀挵(hu谩n)鍔犳垚鑸囬伕鎿囨€ц(gu墨)寰嬶紝蟽-閬风Щ鍙嶆噳(y墨ng)鑸囬伕
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3. 鎺屾彙閫嗗悎鎴愬垎鏋愭柟娉曡ō(sh猫)瑷�(j矛)鍚堟垚璺窔銆�
锛堜笁锛�銆佽€冭│鐨勬柟娉曡垏鑰冭│鏅�(sh铆)闁�
鏈绋嬮噰鐢ㄩ枆鍗疯€冭│锛岃€冭│鏅�(sh铆)闁� 180 鍒嗛悩銆�
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5
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