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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.0K
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.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.0K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.0K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.3K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.3K
Alkyl Halides02:45

Alkyl Halides

19.5K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
19.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.3K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.3K
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

1.6K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
1.6K

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Author Spotlight: Accelerating Discovery in Microporous Material Chemistry
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Author Spotlight: Accelerating Discovery in Microporous Material Chemistry

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フォスファルウミレン:メイングループヘテロサイクルのシントン

Liu Leo Liu1, Jiliang Zhou1, Levy L Cao1

  • 1Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada.

Journal of the American Chemical Society
|September 27, 2019
PubMed
まとめ

3つ組んだアルミニウム・炭素・リン (AlCP) 環を張った新しいフォスファルミリネが合成された. これらの化合物は,リング開きとリング拡大反応を経て,新しい主群ヘテロサイクルを形成する.

科学分野:

  • 有機金属化学
  • メイングループ 化学
  • 合成化学

背景:

  • アルミニウム (I) 複合体は反応性中間物質である.
  • フォスファルキンは合成の際には多用途な構成要素である.
  • 三つ組のリングは,しばしばストレスのためにユニークな反応性を表します.

研究 の 目的:

  • 三つ組のAlCPリングを含む新しいフォスファルウミレンを合成する.
  • これらのストレートされたAlCPシステムの反応性と芳香性を調査する.
  • 新しいメイングループヘテロサイクルの形成を調査する.

主な方法:

  • アルミニウム (I) 複合体とフォスファルキンの間の [1 + 2]サイクロアディション反応.
  • 結晶型フォスファルウミレン化合物の合成
  • 機械的な洞察のための密度関数理論 (DFT) の計算.
  • 各種基質 (アルコール,イソシアン化物,カルベン,カルコゲン,カルボニル,ニトリル) との反応により,環開きと環拡大を研究する.

主要な成果:

  • フォスファルミリネスの合成 HC[(CMe) ((NDipp) ]2Al[C(R) P] (2と3).

さらに関連する動画

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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  • AlCPリングにおける2π電子の芳香性に関する計算的証拠.
  • 化合物3の環開きで,フォスファルケーン4を生成する.
  • 様々な反応剤 (CyNC,BAC,Se,Ph2CO,PhCHCHCOPh,PhCN) で化合物3の簡単なリング拡大により,前例のない主群ヘテロサイクル5−10が形成される.
  • 新しく形成されたヘテロサイクルにおけるCP不飽和結合の保存.
  • 結論:

    • ストレートされたAlCPリングを持つフォスファルウミレーンは, [1 + 2]サイクロアディションでアクセスできます.
    • AlCPリングは芳香性を持ち,様々なリング開きとリング拡大反応を経験します.
    • この化学反応は,CP結合を保持した新しいメイングループヘテロサイクルへのアクセスを提供します.