与结合的二 ((水)) 类吸附物Cy3P=O·(HOO)2CHR (R = 基) 的类型
Rahym Ashirov1, Maya Todorovic1, Nattamai Bhuvanesh1
1Department of Chemistry, Texas A&M University, College Station, TX 77842-3012, USA.
Molecules (Basel, Switzerland)
|January 25, 2025
概括
合成了新的氧化与二氧化氧化的添加物. 这些稳定,固体过氧化物易于处理,并显示出合成化学应用的潜力.
科学领域:
- 有机化学 有机化学
- 超分子化学 超分子化学
- 材料科学 材料科学 材料科学
背景情况:
- 氨酸氧化物是有机合成中的多功能化合物.
- 氧化物是具有各种应用的活性氧物种.
- 吸管形成可以稳定反应性物种并修改它们的特性.
研究的目的:
- 合成和表征氧化的新型二氧化氧化添加物.
- 研究这些添加物的结构,光谱和化学特性.
- 探索它们在合成化学中的潜在应用.
主要方法:
- 使用三氧化物和相应的化物合成了五种新型添加物.
- 完整的表征包括可溶性,结晶,单晶X射线衍射,31P NMR和IR光谱.
- 对6对三的氧化能力的评估.
主要成果:
- 成功合成和表征了五种稳定,晶状的氧化与二氧化氧化的添加物.
- X射线晶体学揭示了具有独特结构特征的结合1:1 adducts.
- 光谱数据 (31P NMR,IR) 表明由于结合而导致的P=O键被削弱.
- 阿德克特6证明了PPh3的选择性氧化到OPPh3的选择性氧化,并进行了非门的改造.
结论:
- 素氧化物的新型二氧化添加物是稳定的,易于处理的,可溶性的固体.
- 键在稳定这些附加物和影响它们的电子性质方面发挥着至关重要的作用.
- 这些添加物代表了合成化学新一类有希望的试剂,在易于使用和可控反应性方面具有优势.
相关概念视频
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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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02:41Formation of Halohydrin from Alkenes
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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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03:08Hydroboration-Oxidation of Alkenes
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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02:38Electrophilic Addition to Alkynes: Halogenation
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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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