Hydroboration–oxidation reaction (original) (raw)
在有机化学中，硼氢化-氧化反应是烯烃与硼烷加成，再被氧化生成醇的两步有机化学反应。 氢和羟基通过顺式加成生成顺式产物。硼氢化-氧化反应是一个反马氏反应，羟基加成到取代基较少的碳上。在有机合成中，这是一个常用的反应。 反应一般按如下形式进行： 该反应常用四氢呋喃（THF）作为溶剂，有时也用其他的极性非质子溶剂。它分为两步：在第一步中，甲硼烷（BH3）与双键加成生成烷基硼，称为烯烃的硼氢化反应。第二步中，烷基硼在碱性条件下与过氧化氢作用生成醇，BH2基团被氧化为羟基，这一步称为烷基硼的氧化反应。
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| dbo:abstract | Hydroboračně–oxidační reakce je dvoukroková hydratační reakce, při níž se alkeny mění na alkoholy. Dochází přitom k vodíku a hydroxylové skupiny na místo, kde se nacházela dvojná vazba. Hydroborace–oxidace probíhají proti Markovnikovovu pravidlu, hydroxyl se navazuje na méně substituovaný uhlík. Reakce je tak stereospecifičtější a pravidelnější obdobou jiných hydratačních reakcí, jako jsou kysele katalyzovaná adice a oxymerkurace-redukce. Hydroborace-oxidace objevil Herbert C. Brown v 50. letech 20. století, za což v roce 1979 obdržel Nobelovu cenu za chemii. Obecný průběh reakce je znázorněn na tomto obrázku: Nejčastějším rozpouštědlem při hydroboračně-oxidačních reakcích je tetrahydrofuran (THF). (cs) Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979. The general form of the reaction is as follows: Tetrahydrofuran (THF) is the archetypal solvent used for hydroboration. (en) De hydroborering-oxidatiereactie, ook wel oxidatieve hydroborering genoemd, is een organische reactie, bestaande uit twee stappen, die een alkeen omzet in een alcohol door de additie van water over de dubbele binding, met een boraan als elektrofiel. De hydroborering-oxidatiereactie is een anti-Markovnikov-reactie, waarbij de hydroxylgroep op het minst gesubstitueerde koolstofatoom van de dubbele binding wordt geplaatst.De reactie werd ontdekt door Herbert Brown in de jaren '50 van de 20e eeuw en werd beloond met de Nobelprijs voor de Scheikunde in 1979. Ze wordt ook wel aangeduid als de Brown-hydroborering. Een voorbeeld van deze reactie is de reactie van 2-methylpropeen tot 2-methylpropan-1-ol: Hierin staat THF voor tetrahydrofuraan, het oplosmiddel waarop boraan stabiel bewaard kan worden. (nl) 在有机化学中，硼氢化-氧化反应是烯烃与硼烷加成，再被氧化生成醇的两步有机化学反应。 氢和羟基通过顺式加成生成顺式产物。硼氢化-氧化反应是一个反马氏反应，羟基加成到取代基较少的碳上。在有机合成中，这是一个常用的反应。 反应一般按如下形式进行： 该反应常用四氢呋喃（THF）作为溶剂，有时也用其他的极性非质子溶剂。它分为两步：在第一步中，甲硼烷（BH3）与双键加成生成烷基硼，称为烯烃的硼氢化反应。第二步中，烷基硼在碱性条件下与过氧化氢作用生成醇，BH2基团被氧化为羟基，这一步称为烷基硼的氧化反应。 (zh) |
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| rdfs:comment | 在有机化学中，硼氢化-氧化反应是烯烃与硼烷加成，再被氧化生成醇的两步有机化学反应。 氢和羟基通过顺式加成生成顺式产物。硼氢化-氧化反应是一个反马氏反应，羟基加成到取代基较少的碳上。在有机合成中，这是一个常用的反应。 反应一般按如下形式进行： 该反应常用四氢呋喃（THF）作为溶剂，有时也用其他的极性非质子溶剂。它分为两步：在第一步中，甲硼烷（BH3）与双键加成生成烷基硼，称为烯烃的硼氢化反应。第二步中，烷基硼在碱性条件下与过氧化氢作用生成醇，BH2基团被氧化为羟基，这一步称为烷基硼的氧化反应。 (zh) Hydroboračně–oxidační reakce je dvoukroková hydratační reakce, při níž se alkeny mění na alkoholy. Dochází přitom k vodíku a hydroxylové skupiny na místo, kde se nacházela dvojná vazba. Hydroborace–oxidace probíhají proti Markovnikovovu pravidlu, hydroxyl se navazuje na méně substituovaný uhlík. Reakce je tak stereospecifičtější a pravidelnější obdobou jiných hydratačních reakcí, jako jsou kysele katalyzovaná adice a oxymerkurace-redukce. Hydroborace-oxidace objevil Herbert C. Brown v 50. letech 20. století, za což v roce 1979 obdržel Nobelovu cenu za chemii. (cs) Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979. (en) De hydroborering-oxidatiereactie, ook wel oxidatieve hydroborering genoemd, is een organische reactie, bestaande uit twee stappen, die een alkeen omzet in een alcohol door de additie van water over de dubbele binding, met een boraan als elektrofiel. De hydroborering-oxidatiereactie is een anti-Markovnikov-reactie, waarbij de hydroxylgroep op het minst gesubstitueerde koolstofatoom van de dubbele binding wordt geplaatst.De reactie werd ontdekt door Herbert Brown in de jaren '50 van de 20e eeuw en werd beloond met de Nobelprijs voor de Scheikunde in 1979. Ze wordt ook wel aangeduid als de Brown-hydroborering. (nl) |
| rdfs:label | Hydroboračně-oxidační reakce (cs) Hydroboration–oxidation reaction (en) Hydroborering-oxidatie (nl) 硼氢化-氧化反应 (zh) |
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