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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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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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.
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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,...
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Alkyl Halides02:45

Alkyl Halides

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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...
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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.
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Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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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.
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Phosphaaluminirenes: Synthons for Main Group Heterocycles.

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
Summary

New phosphaaluminirenes with a strained three-membered aluminum-carbon-phosphorus (AlCP) ring were synthesized. These compounds undergo ring-opening and ring-enlargement reactions, forming novel main group heterocycles.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Synthetic Chemistry

Background:

  • Aluminum(I) complexes are reactive intermediates.
  • Phosphaalkynes are versatile building blocks in synthesis.
  • Three-membered rings often exhibit unique reactivity due to strain.

Purpose of the Study:

  • To synthesize novel phosphaaluminirenes containing a three-membered AlCP ring.
  • To investigate the reactivity and aromaticity of these strained AlCP systems.
  • To explore the formation of new main group heterocycles.

Main Methods:

  • [1 + 2] cycloaddition reaction between an aluminum(I) complex and phosphaalkynes.
  • Synthesis of crystalline phosphaaluminirene compounds.
  • Density functional theory (DFT) calculations for mechanistic insights.
  • Reactions with various substrates (alcohols, isocyanides, carbenes, chalcogens, carbonyls, nitriles) to study ring-opening and ring-enlargement.

Main Results:

  • Synthesis of phosphaaluminirenes HC[(CMe)(NDipp)]2Al[C(R)═P] (2 and 3).
  • Computational evidence for 2π-electron aromaticity in the AlCP ring.
  • Ring-opening of compound 3 upon protonation to yield phosphaalkene 4.
  • Facile ring enlargement of compound 3 with diverse reagents (CyNC, BAC, Se, Ph2CO, PhCH═CHCOPh, PhCN) to form unprecedented main group heterocycles 5-10.
  • Preservation of the C═P unsaturated bond in the newly formed heterocycles.

Conclusions:

  • Phosphaaluminirenes with strained AlCP rings are accessible via [1 + 2] cycloaddition.
  • The AlCP ring exhibits aromatic character and undergoes diverse ring-opening and ring-enlargement reactions.
  • This chemistry provides access to novel main group heterocycles with intact C═P bonds.