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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

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.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...

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Updated: May 21, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

meso-Aryl-3-alkyl-2-oxachlorins.

Junichi Ogikubo1, Eileen Meehan, James T Engle

  • 1Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.

The Journal of Organic Chemistry
|June 27, 2012
PubMed
Summary

Researchers synthesized novel oxazolochlorins by replacing pyrrole rings in porphyrins. These stable, planar compounds exhibit chlorin-like optical properties, offering a new class of versatile porphyrin derivatives.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

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Published on: February 24, 2015

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07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Porphyrins are vital macrocyclic compounds with diverse applications.
  • Modifying porphyrin structures can tune their photophysical and electronic properties.
  • Replacing pyrrole with oxazole offers a novel synthetic strategy.

Purpose of the Study:

  • To synthesize and characterize novel meso-tetraaryl-3-alkyl-2-oxachlorins.
  • To investigate the optical properties of these new oxazolochlorins.
  • To compare their properties with existing chlorin derivatives.

Main Methods:

  • Synthesis of porpholactones from meso-tetraarylporphyrin.
  • Grignard reagent addition to porpholactones to form oxazolochlorins.
  • Spectroscopic analysis (UV-visible, fluorescence) and X-ray crystallography.

Main Results:

  • Successful synthesis of mono- and bis-alkylated 2-oxachlorins.
  • Oxazolochlorins display chlorin-like UV-visible absorption and fluorescence.
  • X-ray diffraction confirmed planar conformations, indicating intrinsic electronic properties govern optical behavior.

Conclusions:

  • Meso-tetraaryl-3-alkyl-2-oxachlorins represent a new, stable class of chlorin analogs.
  • Their preparation is straightforward, and their optical properties are tunable.
  • These compounds hold potential for applications requiring stable, light-absorbing/emitting macrocycles.