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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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...
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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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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.9K
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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.7K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.7K
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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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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The first boroselenates as new silicate analogues.

Michael Daub1, Harald Hillebrecht

  • 1Institut für Anorganische und Analytische Chemie, Albert-Ludwigs-Universität, Albertstrasse 21, 79104 Freiburg (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 1, 2014
PubMed
Summary

The first boroselenates were synthesized and structurally characterized, revealing analogies to borosulfates and borophosphates. Their crystal structures exhibit diverse arrangements of tetrahedral units, similar to silicates.

Keywords:
alkali metalsboronboroselenatesseleniumstructure determination

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Area of Science:

  • Inorganic Chemistry
  • Solid-State Chemistry
  • Crystal Engineering

Background:

  • Boroselenates are a newly synthesized class of inorganic compounds.
  • Their structural relationship to known borosulfates and borophosphates is investigated.

Purpose of the Study:

  • To synthesize and characterize the first boroselenate compounds.
  • To elucidate the structural diversity of boroselenates based on the boron-to-selenium ratio.
  • To explore topological analogies with other inorganic frameworks.

Main Methods:

  • Single-crystal synthesis via reaction of selenic acid, boric acid, and alkali carbonates.
  • Single-crystal X-ray diffraction for structure determination.
  • Comparative structural analysis with related borate compounds.

Main Results:

  • First synthesis of boroselenates as single crystals.
  • Identification of structural motifs including chains and isolated pentamers.
  • Demonstration of structural analogies to borosulfates, borophosphates, and silicates.
  • Detailed crystallographic data for Rb3[B(SeO4)3], Cs3[B(SeO4)3], HK4[B(SeO4)4], and (H3O)Na6[B(SeO4)4](SeO4).

Conclusions:

  • Boroselenates exhibit a rich structural chemistry analogous to borosulfates and borophosphates.
  • The B/Se ratio dictates the formation of different structural architectures.
  • The apex-sharing connectivity of tetrahedra leads to topological similarities with silicates, suggesting potential for diverse crystal structures.