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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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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.
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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C-H bond functionalization through intramolecular hydride transfer.

Michael C Haibach1, Daniel Seidel

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, NJ 08901 (USA) seidel.rutchem.rutgers.edu http://www.seidel-group.com.

Angewandte Chemie (International Ed. in English)
|April 8, 2014
PubMed
Summary

Intramolecular hydride-transfer reactions, known for over 100 years, are gaining new interest. These reactions offer a sustainable method for C-H bond functionalization through redox-neutral transformations.

Keywords:
CH functionalizationasymmetric catalysiscascade reactionshydride transferredox-neutral reactions

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Area of Science:

  • Organic Chemistry
  • Sustainable Chemistry

Background:

  • Intramolecular hydride-transfer reactions have been known for over a century.
  • These reactions are gaining renewed interest in the scientific community.

Purpose of the Study:

  • To summarize recent advancements in intramolecular hydride-transfer reactions.
  • To highlight key historical contributions to this field.
  • To emphasize the utility of hydride shifts in C-H bond functionalization.

Main Methods:

  • Review of recent literature on intramolecular hydride-transfer reactions.
  • Analysis of historical contributions and key developments.
  • Focus on C-H bond functionalization and sustainable reaction design.

Main Results:

  • Hydride shifts are recognized as a valuable strategy for C-H bond functionalization.
  • The redox-neutral nature of these reactions supports sustainable synthesis.
  • Recent progress showcases the versatility and efficiency of these transformations.

Conclusions:

  • Intramolecular hydride-transfer reactions are a promising area for developing sustainable chemical processes.
  • Continued research in this field is expected to yield further innovations in C-H functionalization.