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Hydroboration-Oxidation of Alkenes03:08

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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 Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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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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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.
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Boragerma[5]pyramidanes via a Germole-to-Borole Rearrangement.

Lukas Bührmann1, Amrit Chandi1, Nadeschda Geibel1

  • 1Institute of Chemistry, Carl von Ossietzky Universität Oldenburg, Carl von Ossietzky-Strasse 9-11, D-26129 Oldenburg, Federal Republic of Germany, European Union.

Inorganic Chemistry
|March 24, 2026
PubMed
Summary
This summary is machine-generated.

Researchers report a new germole-to-borole rearrangement using double salt metathesis. This method yields novel germanium(II) borole complexes, classified as boragerma[5]pyramidanes, with tunable structures and unique electronic properties.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Cluster Chemistry

Background:

  • Germole and borole compounds are important heterocyclic structures.
  • Understanding rearrangements between these systems is key for novel material synthesis.

Purpose of the Study:

  • To explore the germole-to-borole rearrangement.
  • To synthesize and characterize novel germanium(II) borole complexes.
  • To investigate the structural and electronic properties of these complexes.

Main Methods:

  • Double salt metathesis reactions.
  • Synthesis of dipotassium germolediides and substituted boron dihalides.
  • X-ray crystallography and spectroscopic analysis.

Main Results:

  • Successful preparation of Ge(II) borole complexes via germole-to-borole rearrangement.
  • Classification of complexes as boragerma[5]pyramidanes (nido-type clusters).
  • Demonstrated tunability of cluster structure via electronic substituents.
  • Identified σ-donor behavior with limited π-acceptor abilities.
  • Germanium elimination observed upon reduction or reaction with nucleophiles.

Conclusions:

  • The germole-to-borole rearrangement offers a viable route to Ge(II) borole complexes.
  • Boragerma[5]pyramidanes represent a new class of molecular clusters with tunable properties.
  • These complexes can be further functionalized or decomposed to yield borole derivatives.