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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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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.
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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Difunctionalization Processes Enabled by Hexafluoroisopropanol.

Maciej Piejko1, Joseph Moran1,2,3, David Lebœuf1

  • 1Institut de Science et d'Ingénierie Supramoléculaires (ISIS), CNRS UMR 7006, Université de Strasbourg, 8 Allée Gaspard Monge, 67000 Strasbourg, France.

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Summary
This summary is machine-generated.

Hexafluoroisopropanol (HFIP) has enabled challenging chemical reactions by activating substrates and stabilizing intermediates. This review details difunctionalization reactions, including cyclizations and additions, unlocked by HFIP.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Hexafluoroisopropanol (HFIP) is a unique solvent and additive.
  • HFIP activates substrates and stabilizes reactive intermediates.
  • HFIP has gained prominence in synthetic chemistry over the last 5 years.

Purpose of the Study:

  • To review difunctionalization processes enabled by HFIP.
  • To highlight HFIP's role in unlocking challenging chemical transformations.

Main Methods:

  • Focus on reactions involving HFIP.
  • Analysis of cyclization reactions.
  • Analysis of addition reactions to alkenes, alkynes, epoxides, and carbonyls.

Main Results:

  • HFIP facilitates challenging difunctionalization reactions.
  • Introduction of diverse functional groups is achieved.
  • HFIP enables novel synthetic pathways.

Conclusions:

  • HFIP is a powerful tool for synthetic chemists.
  • HFIP expands the scope of difunctionalization reactions.
  • HFIP is crucial for accessing complex molecules.