. . "\u30B7\u30E2\u30F3\u30BA\u30FB\u30B9\u30DF\u30B9\u53CD\u5FDC"@ja . . "Simmons-Smith reaction"@en . . . . . . "Simmons-Smith reaction in progress"@en . . "Reacci\u00F3 de Simmons-Smith"@ca . "Simmons-Smith-Reaktion"@de . . . "Die Simmons-Smith-Reaktion ist eine Namensreaktion in der Organischen Chemie, die nach ihren Entwicklern Howard E. Simmons und benannt wurde. Sie dient der Synthese von Derivaten des Cyclopropans und ist eine Additionsreaktion, wobei ein Carben an eine Doppelbindung addiert wird, ohne dass freies Carben im Reaktionsgemisch vorhanden ist."@de . . . . . . . . . . . "La reacci\u00F3 de Simmons-Smith \u00E9s una reacci\u00F3 org\u00E0nica en la qual un reacciona amb un alqu\u00E8 (o un alqu\u00ED) per a formar un cicloprop\u00E0. Com m\u00E9s gran sigui la densitat electr\u00F2nica de l'alqu\u00E8 m\u00E9s afavorida estar\u00E0 la formaci\u00F3 del cicloprop\u00E0. Una altra opci\u00F3 per l'obtenci\u00F3 de ciclopropans \u00E9s la ciclopropanaci\u00F3 per descomposici\u00F3 de diazocompostos. Va ser descoberta pels qu\u00EDmics i l'any 1958."@ca . "La sintesi di Simmons-Smith permette di ottenere facilmente con buone rese anelli ciclopropanici sostituiti a partire da alcheni,impiegando CH2I2 e una lega di zinco-rame che costituiscono appunto il reattivo di Simmons-Smith.Si pensa che la specie reattiva sia un intermedio di organozinco di formula ICH2ZnI che pu\u00F2 essere considerato un carbene mascherato (un carbenoide). In questo modo si evita la formazione nell'ambiente di reazione di specie carbeniche libere che altrimenti darebbero anche reazioni di, difficilmente controllabili. La reazione altamente stereospecifica e regioselettiva avviene con un attacco syn concertato e, per una generica olefina, pu\u00F2 essere schematizzata come segue: Uno sviluppo della sintesi di Simmons-Smith prevede il trattamento del substrato, invece che con il semplice diiodometano, con un generico diiododerivatoRCHI2 o ArCHI2 e Et2Zn in etere; in questo modo \u00E8 possibile ottenere ciclopropani ulteriormente funzionalizzati."@it . . "La reacci\u00F3 de Simmons-Smith \u00E9s una reacci\u00F3 org\u00E0nica en la qual un reacciona amb un alqu\u00E8 (o un alqu\u00ED) per a formar un cicloprop\u00E0. Com m\u00E9s gran sigui la densitat electr\u00F2nica de l'alqu\u00E8 m\u00E9s afavorida estar\u00E0 la formaci\u00F3 del cicloprop\u00E0. Una altra opci\u00F3 per l'obtenci\u00F3 de ciclopropans \u00E9s la ciclopropanaci\u00F3 per descomposici\u00F3 de diazocompostos. Va ser descoberta pels qu\u00EDmics i l'any 1958."@ca . "A rea\u00E7\u00E3o de Simmons\u2013Smith \u00E9 uma processo no qual um reage com uma alceno (ou alcino) para formar ciclopropano . Deve seu nome a e R. D. Smith. Por o metileno estar ligado a ambos os carbonos do alceno simultaneamente, a configura\u00E7\u00E3o da liga\u00E7\u00E3o dupla \u00E9 mantida no produto e o processo \u00E9 estereoespec\u00EDfico. Assim, ciclohexeno, diiodometano, e um (como , ICH2ZnI) produz (diciclo[4.1.0]heptano). Alternativamente, pode ser utilizado em lugar do par zinco-cobre.A rea\u00E7\u00E3o est\u00E1 geralmente sujeita a efeitos est\u00E9ricos, e ent\u00E3o ciclopropana\u00E7\u00E3o usualmente ocorre na face mais oculta. De qualquer forma, quando u hidroxi-substituinte est\u00E1 presente no substrato em proximidade \u00E0 liga\u00E7\u00E3o dupla, o zinco se coordena com o hidroxi-substituinte, direcionando a ciclopropana\u00E7\u00E3o cis para o grupo hidroxil (o que pode n\u00E3o corresponder \u00E0 ciclopropana\u00E7\u00E3o da face mais estericamente acess\u00EDvel da liga\u00E7\u00E3o dupla): O reagente de Simmons\u2013Smith, por exemplo diiodometano e dietilzinco, pode reagir com tioet\u00E9res para gerar de enxofre, o que subsequentemente leva a um , e n\u00E3o ciclopropana\u00E7\u00E3o de alceno na mesma mol\u00E9cula, a menos que um excesso de reagente de Simmons-Smith seja usado:"@pt . . . . . . . "23229"^^ . . . . . "Simmons-Smith-reactie"@nl . "\u30B7\u30E2\u30F3\u30BA\u30FB\u30B9\u30DF\u30B9\u53CD\u5FDC\uFF08\u30B7\u30E2\u30F3\u30BA\u30FB\u30B9\u30DF\u30B9\u306F\u3093\u306E\u3046\u3001\u82F1: Simmons\u2013Smith reaction\uFF09\u306F\u30B8\u30CF\u30ED\u30A2\u30EB\u30AB\u30F3\u306B\u3088\u308A\u30A2\u30EB\u30B1\u30F3\u3092\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u5316\u3059\u308B\u5316\u5B66\u53CD\u5FDC\u306E\u3053\u3068\u3067\u3042\u308B\u3002 1958\u5E74\u306B\u30CF\u30EF\u30FC\u30C9\u30FB\u30B7\u30E2\u30F3\u30BA\u30FB\u30B8\u30E5\u30CB\u30A2\u3068\u30ED\u30CA\u30EB\u30C9\u30FB\u30B9\u30DF\u30B9\u306B\u3088\u3063\u3066\u5831\u544A\u3055\u308C\u305F\u3002\u3082\u3063\u3068\u3082\u521D\u671F\u306B\u7528\u3044\u3089\u308C\u305F\u65B9\u6CD5\u306F\u3001\u5869\u9178\u3067\u8868\u9762\u3092\u6D17\u6D44\u3057\u3066\u6D3B\u6027\u5316\u3057\u305F\u4E9C\u925B\u7C89\u672B\u306B\u786B\u9178\u9285\u6C34\u6EB6\u6DB2\u3092\u4F5C\u7528\u3055\u305B\u308B\u3053\u3068\u3067\u8ABF\u88FD\u3055\u308C\u308B\u4E9C\u925B\u2013\u9285\u30AB\u30C3\u30D7\u30EB\u306E\u5B58\u5728\u4E0B\u3001\u30A2\u30EB\u30B1\u30F3\u306B\u30A8\u30FC\u30C6\u30EB\u7CFB\u6EB6\u5A92\u4E2D\u3067\u30B8\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u3092\u52A0\u3048\u308B\u65B9\u6CD5\u3067\u3042\u308B\u3002\u305D\u306E\u5F8C\u3001\u4E9C\u925B\u306E\u4EE3\u308F\u308A\u306B\u30B8\u30A8\u30C1\u30EB\u4E9C\u925B\u3092\u4F7F\u7528\u3059\u308B\u6539\u826F\u6CD5\u304C1966\u5E74\u306B\u53E4\u5DDD\u3089\u306B\u3088\u3063\u3066\u5831\u544A\u3055\u308C\u3001\u3053\u3061\u3089\u306E\u65B9\u6CD5\u304C\u3088\u308A\u4E00\u822C\u7684\u3068\u306A\u3063\u305F\u3002 \u53CD\u5FDC\u6A5F\u69CB\u306F\u4E9C\u925B\u306B\u30B8\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u304C\u9178\u5316\u7684\u4ED8\u52A0\u3057\u3066\u751F\u6210\u3059\u308B ICH2ZnI \u3068\u3044\u3046\u5316\u5B66\u7A2E\u304C\u30A2\u30EB\u30B1\u30F3\u3068\u53CD\u5FDC\u3059\u308B\u3082\u306E\u3068\u8003\u3048\u3089\u308C\u3066\u3044\u308B\u3002\u3053\u306E\u3088\u3046\u306A\u6709\u6A5F\u91D1\u5C5E\u5316\u5B66\u7A2E\u306F\u53CD\u5FDC\u4E0A\u30AB\u30EB\u30D9\u30F3\u306E\u7B49\u4FA1\u4F53\u3068\u8003\u3048\u3089\u308C\u308B\u3053\u3068\u304B\u3089\u30AB\u30EB\u30D9\u30CE\u30A4\u30C9\u3068\u7DCF\u79F0\u3055\u308C\u308B\u3002\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u74B0\u306E\u65B0\u305F\u306B\u751F\u6210\u3059\u308B2\u3064\u306E\u03C3\u7D50\u5408\u306F\u5354\u594F\u7684\u306B\u751F\u6210\u3059\u308B\u3002\u305D\u306E\u305F\u3081\u3001cis-\u30A2\u30EB\u30B1\u30F3\u304B\u3089\u306F cis \u7F6E\u63DB\u306E\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u304C\u3001trans-\u30A2\u30EB\u30B1\u30F3\u304B\u3089\u306F trans \u7F6E\u63DB\u306E\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u304C\u5F97\u3089\u308C\u308B\u7ACB\u4F53\u7279\u7570\u7684\u306A\u53CD\u5FDC\u3068\u306A\u308B\u3002"@ja . . . "La r\u00E9action de Simmons-Smith est une m\u00E9thode de pr\u00E9paration st\u00E9r\u00E9osp\u00E9cifique de compos\u00E9s de type cyclopropane. Cette r\u00E9action met en jeu un alc\u00E8ne, du diiodom\u00E9thane, ainsi que du zinc m\u00E9tallique. Elle a \u00E9t\u00E9 d\u00E9crite pour la premi\u00E8re fois par Simmons et Smith en 1958."@fr . . "Rea\u00E7\u00E3o de Simmons-Smith"@pt . . . . . "\u897F\u8499\u65AF\u2013\u53F2\u5BC6\u65AF\u53CD\u5E94"@zh . . . . . . "Simmons\u2013Smith reaction"@en . . . . . . . . . . . . "\u30B7\u30E2\u30F3\u30BA\u30FB\u30B9\u30DF\u30B9\u53CD\u5FDC\uFF08\u30B7\u30E2\u30F3\u30BA\u30FB\u30B9\u30DF\u30B9\u306F\u3093\u306E\u3046\u3001\u82F1: Simmons\u2013Smith reaction\uFF09\u306F\u30B8\u30CF\u30ED\u30A2\u30EB\u30AB\u30F3\u306B\u3088\u308A\u30A2\u30EB\u30B1\u30F3\u3092\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u5316\u3059\u308B\u5316\u5B66\u53CD\u5FDC\u306E\u3053\u3068\u3067\u3042\u308B\u3002 1958\u5E74\u306B\u30CF\u30EF\u30FC\u30C9\u30FB\u30B7\u30E2\u30F3\u30BA\u30FB\u30B8\u30E5\u30CB\u30A2\u3068\u30ED\u30CA\u30EB\u30C9\u30FB\u30B9\u30DF\u30B9\u306B\u3088\u3063\u3066\u5831\u544A\u3055\u308C\u305F\u3002\u3082\u3063\u3068\u3082\u521D\u671F\u306B\u7528\u3044\u3089\u308C\u305F\u65B9\u6CD5\u306F\u3001\u5869\u9178\u3067\u8868\u9762\u3092\u6D17\u6D44\u3057\u3066\u6D3B\u6027\u5316\u3057\u305F\u4E9C\u925B\u7C89\u672B\u306B\u786B\u9178\u9285\u6C34\u6EB6\u6DB2\u3092\u4F5C\u7528\u3055\u305B\u308B\u3053\u3068\u3067\u8ABF\u88FD\u3055\u308C\u308B\u4E9C\u925B\u2013\u9285\u30AB\u30C3\u30D7\u30EB\u306E\u5B58\u5728\u4E0B\u3001\u30A2\u30EB\u30B1\u30F3\u306B\u30A8\u30FC\u30C6\u30EB\u7CFB\u6EB6\u5A92\u4E2D\u3067\u30B8\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u3092\u52A0\u3048\u308B\u65B9\u6CD5\u3067\u3042\u308B\u3002\u305D\u306E\u5F8C\u3001\u4E9C\u925B\u306E\u4EE3\u308F\u308A\u306B\u30B8\u30A8\u30C1\u30EB\u4E9C\u925B\u3092\u4F7F\u7528\u3059\u308B\u6539\u826F\u6CD5\u304C1966\u5E74\u306B\u53E4\u5DDD\u3089\u306B\u3088\u3063\u3066\u5831\u544A\u3055\u308C\u3001\u3053\u3061\u3089\u306E\u65B9\u6CD5\u304C\u3088\u308A\u4E00\u822C\u7684\u3068\u306A\u3063\u305F\u3002 \u53CD\u5FDC\u6A5F\u69CB\u306F\u4E9C\u925B\u306B\u30B8\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u304C\u9178\u5316\u7684\u4ED8\u52A0\u3057\u3066\u751F\u6210\u3059\u308B ICH2ZnI \u3068\u3044\u3046\u5316\u5B66\u7A2E\u304C\u30A2\u30EB\u30B1\u30F3\u3068\u53CD\u5FDC\u3059\u308B\u3082\u306E\u3068\u8003\u3048\u3089\u308C\u3066\u3044\u308B\u3002\u3053\u306E\u3088\u3046\u306A\u6709\u6A5F\u91D1\u5C5E\u5316\u5B66\u7A2E\u306F\u53CD\u5FDC\u4E0A\u30AB\u30EB\u30D9\u30F3\u306E\u7B49\u4FA1\u4F53\u3068\u8003\u3048\u3089\u308C\u308B\u3053\u3068\u304B\u3089\u30AB\u30EB\u30D9\u30CE\u30A4\u30C9\u3068\u7DCF\u79F0\u3055\u308C\u308B\u3002\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u74B0\u306E\u65B0\u305F\u306B\u751F\u6210\u3059\u308B2\u3064\u306E\u03C3\u7D50\u5408\u306F\u5354\u594F\u7684\u306B\u751F\u6210\u3059\u308B\u3002\u305D\u306E\u305F\u3081\u3001cis-\u30A2\u30EB\u30B1\u30F3\u304B\u3089\u306F cis 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\u307E\u305F\u53CD\u5FDC\u3059\u308B\u4E8C\u91CD\u7D50\u5408\u306E\u8FD1\u508D\u306B\u30D2\u30C9\u30ED\u30AD\u30B7\u57FA\u306A\u3069\u306E\u4E9C\u925B\u306B\u914D\u4F4D\u53EF\u80FD\u306A\u9178\u7D20\u5B98\u80FD\u57FA\u304C\u5B58\u5728\u3059\u308B\u5834\u5408\u3001\u30AB\u30EB\u30D9\u30CE\u30A4\u30C9\u304C\u9178\u7D20\u5B98\u80FD\u57FA\u306B\u914D\u4F4D\u3057\u3066\u304B\u3089\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u5316\u304C\u8D77\u3053\u308B\u305F\u3081\u3001\u4E8C\u91CD\u7D50\u5408\u306E\u9178\u7D20\u5B98\u80FD\u57FA\u304C\u3042\u308B\u5074\u306E\u9762\u3067\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u74B0\u304C\u5F62\u6210\u3055\u308C\u308B\u7ACB\u4F53\u9078\u629E\u7684\u306A\u53CD\u5FDC\u3068\u306A\u308B\u3002 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\u305D\u306E\u4ED6\u3001\u3088\u308A\u6D3B\u6027\u306A\u30B5\u30DE\u30EA\u30A6\u30E0\u3092\u4F7F\u7528\u3059\u308B\u65B9\u6CD5\u3084\u30C8\u30EA\u30A8\u30C1\u30EB\u30A2\u30EB\u30DF\u30CB\u30A6\u30E0\u3092\u4F7F\u7528\u3059\u308B\u65B9\u6CD5\u3082\u5831\u544A\u3055\u308C\u3066\u3044\u308B\u3002\u4F7F\u7528\u3055\u308C\u308B\u30B8\u30CF\u30ED\u30A2\u30EB\u30AB\u30F3\u306F\u30B8\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u304C\u5831\u544A\u3055\u308C\u308B\u53CD\u5FDC\u306E\u5927\u90E8\u5206\u3092\u5360\u3081\u3066\u3044\u308B\u304C\u30011,1-\u30B8\u30E8\u30FC\u30C9\u30A2\u30EB\u30AB\u30F3\u306A\u3089\u3044\u305A\u308C\u3082\u53CD\u5FDC\u306B\u4F7F\u7528\u3067\u304D\u308B\u3002\u30B8\u30D6\u30ED\u30E2\u30E1\u30BF\u30F3\u306F\u8D85\u97F3\u6CE2\u306E\u4F7F\u7528\u3084\u5869\u5316\u30A2\u30BB\u30C1\u30EB\u306A\u3069\u306E\u5171\u5B58\u4E0B\u3067\u53CD\u5FDC\u306B\u4F7F\u7528\u3067\u304D\u308B\u5831\u544A\u304C\u3042\u308B\u3002\u30AF\u30ED\u30ED\u30E8\u30FC\u30C9\u30E1\u30BF\u30F3\u306F\u30B5\u30DE\u30EA\u30A6\u30E0\u3067\u306E\u53CD\u5FDC\u3067\u4F7F\u7528\u3067\u304D\u308B\u3002\u307E\u305F\u53CD\u5FDC\u306E\u6D3B\u6027\u7A2E\u306F ICH2ZnI \u3067\u3042\u308B\u305F\u3081\u3001\u30B8\u30CF\u30ED\u30A2\u30EB\u30AB\u30F3\u3092\u4F7F\u7528\u3057\u306A\u304F\u3068\u3082\u3053\u306E\u6D3B\u6027\u7A2E\u3092\u751F\u6210\u3055\u305B\u308C\u3070\u540C\u69D8\u306E\u30B7\u30AF\u30ED\u30D7\u30ED\u30D1\u30F3\u5316\u3092\u884C\u306A\u3046\u3053\u3068\u304C\u3067\u304D\u308B\u3002\u3053\u306E\u3088\u3046\u306A\u65B9\u6CD5\u3068\u3057\u3066\u30B8\u30A2\u30BE\u30E1\u30BF\u30F3\u3068\u30E8\u30A6\u5316\u4E9C\u925B\u3092\u53CD\u5FDC\u3055\u305B\u308B\u65B9\u6CD5\u304C\u3042\u308B\u3002"@ja . . . . . . . . . . . "La sintesi di Simmons-Smith permette di ottenere facilmente con buone rese anelli ciclopropanici sostituiti a partire da alcheni,impiegando CH2I2 e una lega di zinco-rame che costituiscono appunto il reattivo di Simmons-Smith.Si pensa che la specie reattiva sia un intermedio di organozinco di formula ICH2ZnI che pu\u00F2 essere considerato un carbene mascherato (un carbenoide). In questo modo si evita la formazione nell'ambiente di reazione di specie carbeniche libere che altrimenti darebbero anche reazioni di, difficilmente controllabili."@it . . . "Simmons\u2013Smith\u53CD\u5E94\uFF08\u897F\u8499\u65AF\uFF0D\u53F2\u5BC6\u65AF\u53CD\u5E94\uFF09\u662F\u70EF\u70C3\u6216\u7094\u70C3\u4E0E\u53D1\u751F\u53CD\u5E94\u751F\u6210\u73AF\u4E19\u70F7\u73AF\u7CFB\u7684\u6709\u673A\u53CD\u5E94\u3002 \u6B64\u53CD\u5E94\u4EE5\u53D1\u73B0\u8005\u548CR. D. Smith\u547D\u540D\u3002 \u8FD9\u4E2A\u53CD\u5E94\u7528\u5230\u7684\u7C7B\u5361\u5BBE\u8BD5\u5242\u79F0\u4E3ASimmons-Smith\u8BD5\u5242\uFF0C\u662F\u4E2A\u6709\u673A\u950C\u5316\u5408\u7269\uFF0C\u901A\u5F0FX(CR1R2)ZnY\uFF0C\u4E00\u822C\u4E3A\uFF08ICH2ZnI\uFF09\u3002\u5B83\u4E00\u822C\u901A\u8FC71,1-\u4E8C\u5364\u5316\u7269\u4E0E\u950C\u94DC\u5076\uFF08Zn(Cu)\uFF09\u5728\u919A\u7C7B\u6EB6\u5242\u4E2D\u53CD\u5E94\u5236\u53D6\u3002\u6700\u5E38\u7528\u76841,1-\u4E8C\u5364\u4EE3\u70C3\u4E3A\u4E8C\u5364\u7532\u70F7\uFF0C\u5982\u4E8C\u7898\u7532\u70F7\u3002\u950C\u94DC\u5076\u7531\u950C\u7C89\u5728\u786B\u9178\u94DC\u7684\u9178\u6027\u6EB6\u6DB2\u4E2D\u5904\u7406\u6D3B\u5316\u800C\u5F97\u3002\u4E5F\u53EF\u4EE5\u7528\u4E8C\u4E59\u57FA\u950C\u4EE3\u66FF\u950C\u94DC\u5076\u3002 \u53CD\u5E94\u4E2DSimmons-Smith\u8BD5\u5242\u53EF\u4EE5\u63D0\u524D\u5236\u53D6\uFF0C\u4E5F\u53EF\u4EE5\u5728\u53CD\u5E94\u4E2D\u539F\u4F4D\u751F\u6210\u800C\u53C2\u52A0\u53CD\u5E94\u3002\u4E0E\u683C\u6C0F\u8BD5\u5242\u7684\u7C7B\u4F3C\uFF0CSimmons-Smith\u8BD5\u5242\u4E5F\u5B58\u5728\u5982\u4E0B\u5E73\u8861\uFF1A"@zh . "R\u00E9action de Simmons-Smith"@fr . . . . . . . . . . . . . . . . . . . . "De Simmons-Smith-reactie of Simmons-Smith-cyclopropanatie is een cheletrope reactie, waarbij een carbeen reageert met een alkeen of alkyn ter vorming van een cyclopropaanring. De bron voor het carbeen is doorgaans di-joodmethaan, dat in een inert oplosmiddel (veelal di-ethylether of dichloormethaan) in reactie wordt gebracht met een legering van zink en koper (het zogenaamd zink-koper-koppel):"@nl . . . . . . "Sintesi di Simmons-Smith"@it . "La r\u00E9action de Simmons-Smith est une m\u00E9thode de pr\u00E9paration st\u00E9r\u00E9osp\u00E9cifique de compos\u00E9s de type cyclopropane. Cette r\u00E9action met en jeu un alc\u00E8ne, du diiodom\u00E9thane, ainsi que du zinc m\u00E9tallique. Elle a \u00E9t\u00E9 d\u00E9crite pour la premi\u00E8re fois par Simmons et Smith en 1958."@fr . . . "Ring forming reaction"@en . . . . . . . . . . . . . . . . . . . . . . . . . . "Ronald D. Smith"@en . . . . . . . . . . . . . "Die Simmons-Smith-Reaktion ist eine Namensreaktion in der Organischen Chemie, die nach ihren Entwicklern Howard E. Simmons und benannt wurde. Sie dient der Synthese von Derivaten des Cyclopropans und ist eine Additionsreaktion, wobei ein Carben an eine Doppelbindung addiert wird, ohne dass freies Carben im Reaktionsgemisch vorhanden ist."@de . . . . . . . "Simmonsova\u2013Smithova reakce"@cs . . . . . "The Simmons\u2013Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and . It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific. Thus, cyclohexene, diiodomethane, and a zinc-copper couple (as iodomethylzinc iodide, ICH2ZnI) yield norcarane (bicyclo[4.1.0]heptane)."@en . . . "The Simmons\u2013Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and . It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific. Thus, cyclohexene, diiodomethane, and a zinc-copper couple (as iodomethylzinc iodide, ICH2ZnI) yield norcarane (bicyclo[4.1.0]heptane). The Simmons\u2013Smith reaction is generally preferred over other methods of cyclopropanation, however it can be expensive due to the high cost of diiodomethane. Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The reactivity of the system can also be increased by using the Furukawa modification, exchanging the zinc\u2011copper couple for diethylzinc. The Simmons\u2013Smith reaction is generally subject to steric effects, and thus cyclopropanation usually takes place on the less hindered face. However, when a hydroxy substituent is present in the substrate in proximity to the double bond, the zinc coordinates with the hydroxy substituent, directing cyclopropanation cis to the hydroxyl group (which may not correspond to cyclopropanation of the sterically most accessible face of the double bond): An interactive 3D model of this reaction can be seen at ChemTube3D."@en . . . . . . . "A rea\u00E7\u00E3o de Simmons\u2013Smith \u00E9 uma processo no qual um reage com uma alceno (ou alcino) para formar ciclopropano . Deve seu nome a e R. D. Smith. Por o metileno estar ligado a ambos os carbonos do alceno simultaneamente, a configura\u00E7\u00E3o da liga\u00E7\u00E3o dupla \u00E9 mantida no produto e o processo \u00E9 estereoespec\u00EDfico. Assim, ciclohexeno, diiodometano, e um (como , ICH2ZnI) produz (diciclo[4.1.0]heptano)."@pt . . . . "Simmons\u2013Smith\u53CD\u5E94\uFF08\u897F\u8499\u65AF\uFF0D\u53F2\u5BC6\u65AF\u53CD\u5E94\uFF09\u662F\u70EF\u70C3\u6216\u7094\u70C3\u4E0E\u53D1\u751F\u53CD\u5E94\u751F\u6210\u73AF\u4E19\u70F7\u73AF\u7CFB\u7684\u6709\u673A\u53CD\u5E94\u3002 \u6B64\u53CD\u5E94\u4EE5\u53D1\u73B0\u8005\u548CR. D. Smith\u547D\u540D\u3002 \u8FD9\u4E2A\u53CD\u5E94\u7528\u5230\u7684\u7C7B\u5361\u5BBE\u8BD5\u5242\u79F0\u4E3ASimmons-Smith\u8BD5\u5242\uFF0C\u662F\u4E2A\u6709\u673A\u950C\u5316\u5408\u7269\uFF0C\u901A\u5F0FX(CR1R2)ZnY\uFF0C\u4E00\u822C\u4E3A\uFF08ICH2ZnI\uFF09\u3002\u5B83\u4E00\u822C\u901A\u8FC71,1-\u4E8C\u5364\u5316\u7269\u4E0E\u950C\u94DC\u5076\uFF08Zn(Cu)\uFF09\u5728\u919A\u7C7B\u6EB6\u5242\u4E2D\u53CD\u5E94\u5236\u53D6\u3002\u6700\u5E38\u7528\u76841,1-\u4E8C\u5364\u4EE3\u70C3\u4E3A\u4E8C\u5364\u7532\u70F7\uFF0C\u5982\u4E8C\u7898\u7532\u70F7\u3002\u950C\u94DC\u5076\u7531\u950C\u7C89\u5728\u786B\u9178\u94DC\u7684\u9178\u6027\u6EB6\u6DB2\u4E2D\u5904\u7406\u6D3B\u5316\u800C\u5F97\u3002\u4E5F\u53EF\u4EE5\u7528\u4E8C\u4E59\u57FA\u950C\u4EE3\u66FF\u950C\u94DC\u5076\u3002 \u53CD\u5E94\u4E2DSimmons-Smith\u8BD5\u5242\u53EF\u4EE5\u63D0\u524D\u5236\u53D6\uFF0C\u4E5F\u53EF\u4EE5\u5728\u53CD\u5E94\u4E2D\u539F\u4F4D\u751F\u6210\u800C\u53C2\u52A0\u53CD\u5E94\u3002\u4E0E\u683C\u6C0F\u8BD5\u5242\u7684\u7C7B\u4F3C\uFF0CSimmons-Smith\u8BD5\u5242\u4E5F\u5B58\u5728\u5982\u4E0B\u5E73\u8861\uFF1A"@zh . . . . . "De Simmons-Smith-reactie of Simmons-Smith-cyclopropanatie is een cheletrope reactie, waarbij een carbeen reageert met een alkeen of alkyn ter vorming van een cyclopropaanring. De bron voor het carbeen is doorgaans di-joodmethaan, dat in een inert oplosmiddel (veelal di-ethylether of dichloormethaan) in reactie wordt gebracht met een legering van zink en koper (het zogenaamd zink-koper-koppel): De reactie werd vernoemd naar de Amerikaanse scheikundigen en , die ze in 1958 publiceerden. Het is voor de organische scheikundige een van de belangrijkste methoden voor de vorming van cyclopropaanringen."@nl . . . . . . "1094545214"^^ . "1693196"^^ . . . . . . . .