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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Alkyl Halides02:45

Alkyl Halides

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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...
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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.
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Sulfondiimidoyl-Containing Hypervalent Iodine(III) Compounds: Synthesis and Reactivity.

Marcus Becker1, Calogero Quaranta1, Marco T Passia1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen 52074, Germany.

The Journal of Organic Chemistry
|January 8, 2026
PubMed
Summary

Researchers synthesized novel N-connected hypervalent iodine(III) compounds from sulfondiimines and methoxy(tosyloxy)iodobenzene (MTIB). These stable compounds are easily isolated and show potential in various organic transformations.

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Area of Science:

  • Organic Chemistry
  • Hypervalent Iodine Chemistry
  • Sulfur-Nitrogen Chemistry

Background:

  • Sulfondiimines are versatile building blocks in organic synthesis.
  • Hypervalent iodine compounds offer unique reactivity for chemical transformations.
  • Development of new synthetic methodologies is crucial for accessing novel chemical structures.

Purpose of the Study:

  • To synthesize unprecedented N-connected hypervalent iodine(III) compounds.
  • To explore the reactivity of these novel compounds in organic transformations.
  • To establish a facile and efficient synthetic route to these new chemical entities.

Main Methods:

  • Reaction of N-monosubstituted sulfondiimines with methoxy(tosyloxy)iodobenzene (MTIB).
  • Isolation of products via simple filtration.
  • Characterization of the synthesized hypervalent iodine(III) compounds.
  • Evaluation of compound reactivity in various organic reactions.

Main Results:

  • High to excellent yields of N-connected hypervalent iodine(III) compounds were achieved.
  • Products were obtained rapidly (3-30 min) and purified by simple filtration.
  • The synthesis tolerated broad variations in sulfondiimine S-substituents (aryl, alkyl).
  • The newly synthesized compounds demonstrated potential in several organic transformations.

Conclusions:

  • A novel and efficient method for synthesizing N-connected hypervalent iodine(III) compounds has been developed.
  • The synthesized compounds are stable, easily accessible, and exhibit diverse reactivity.
  • This work expands the scope of hypervalent iodine chemistry and sulfondiimine applications.