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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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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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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
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Insertion of [1.1.1]propellane into aromatic disulfides.

Robin M Bär1, Gregor Heinrich1, Martin Nieger2

  • 1Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.

Beilstein Journal of Organic Chemistry
|July 12, 2019
PubMed
Summary

This study introduces a new UV-initiated radical reaction for synthesizing bicyclo[1.1.1]pentane (BCP) sulfides from [1.1.1]propellane and disulfides. This method efficiently creates functionalized BCPs, valuable rigid linkers in chemistry.

Keywords:
[1.1.1]propellanebicyclo[1.1.1]pentanebioisosteresdisulfideslinkers

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Bicyclo[1.1.1]pentanes (BCPs) are increasingly recognized for their utility as rigid linkers and bioisosteres of para-substituted benzene and alkyne groups.
  • The synthesis of BCPs is challenging, with limited established methods, driving the need for novel synthetic routes.
  • The [1.1.1]propellane molecule is a key precursor for BCP synthesis, but its reactivity with disulfide bonds remains underexplored.

Purpose of the Study:

  • To develop a novel and efficient method for synthesizing symmetrically and unsymmetrically substituted 1,3-bissulfanylbicyclo[1.1.1]pentanes.
  • To investigate the UV-initiated radical reaction between [1.1.1]propellane and various disulfides.
  • To explore the scope and limitations of this new synthetic approach, including functional group tolerance and product selectivity.

Main Methods:

  • UV-initiated radical reaction between [1.1.1]propellane and disulfides.
  • Optimization of reactant ratios to control product formation (BCP vs. [2]staffane).
  • Purification techniques including column chromatography and preparative TLC.
  • Structural confirmation using single crystal X-ray diffraction.

Main Results:

  • Successful synthesis of symmetrically and unsymmetrically substituted BCP sulfides with yields up to 98%.
  • Demonstrated control over product distribution by adjusting the ratio of [1.1.1]propellane to disulfide, yielding either BCPs or a mixture of BCPs and [2]staffanes.
  • The reaction tolerates a range of functional groups, including halogens, alkyl, and methoxy substituents.
  • Challenging but achievable separation of BCP and [2]staffane products via chromatography.
  • X-ray diffraction confirmed the characteristic rod-like structure of the [2]staffane products.

Conclusions:

  • A novel UV-initiated radical reaction provides an efficient route to functionalized 1,3-bissulfanylbicyclo[1.1.1]pentanes.
  • The method offers control over product selectivity and demonstrates broad functional group compatibility.
  • This work expands the synthetic toolbox for accessing valuable BCP scaffolds and related [2]staffanes for diverse applications.