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Related Concept Videos

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.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Bi(OTf)(3)-Catalyzed 5-Exo-Trig Cyclization via Halide Activation.

Ryuji Hayashi1, Gregory R Cook

  • 1Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, ND 58105.

Tetrahedron Letters
|January 6, 2009
PubMed
Summary

Bismuth triflate activates allyl halides for efficient cationic cyclization of alkenes. This Lewis acid shows unique reactivity, suggesting novel halophilic properties for bismuth salts in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Lewis acids are crucial catalysts in organic synthesis.
  • Allyl halides are versatile synthetic intermediates.
  • Cationic cyclization is a key reaction for forming cyclic compounds.

Purpose of the Study:

  • To investigate the efficacy of bismuth triflate (Bi(OTf)3) as a Lewis acid catalyst.
  • To explore the cationic cyclization of alkenes mediated by Bi(OTf)3.
  • To understand the unique reactivity of bismuth salts in this transformation.

Main Methods:

  • Treatment of alkenes with allyl halides in the presence of Bi(OTf)3.
  • Analysis of reaction products to determine efficiency and selectivity.
  • Comparison of Bi(OTf)3 with other Lewis acids.

Main Results:

  • Bi(OTf)3 efficiently catalyzed the cationic cyclization of alkenes with allyl halides.
  • Bismuth salts exhibited unique reactivity compared to other Lewis acids, especially with less substituted alkenes.
  • The observed reactivity suggests potential halophilic properties of bismuth triflate.

Conclusions:

  • Bismuth triflate is a highly effective catalyst for alkene cyclization.
  • Bismuth triflate displays unique catalytic properties, potentially due to halophilicity.
  • This study opens new avenues for utilizing bismuth compounds in organic synthesis.