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Related Concept Videos

Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

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Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
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Cleavage and Blastulation

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After a large-single-celled zygote is produced via fertilization, the process of cleavage occurs while zygotes travel through the uterine tube. Cleavage is a mitotic cell division that does not result in growth. With each round of successive cell division, daughter cells get increasingly smaller.
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Crown Ethers02:36

Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...
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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
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Alkyl Halides02:45

Alkyl Halides

20.0K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes.

Caleb A H Jones1, Nathan D Schley

  • 1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA. nathan.schley@vanderbilt.edu.

Organic & Biomolecular Chemistry
|November 8, 2018
PubMed
Summary
This summary is machine-generated.

A novel iridium complex enables selective cleavage of ethers to silyl ethers, outperforming previous catalysts. This advancement is crucial for complex molecule synthesis, offering better control in C-O bond activation reactions.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Heterolytic silane activation is key for converting ethers to silyl ethers via C-O bond cleavage.
  • Previous iridium catalysts, particularly pincer-supported ones, exhibit limited selectivity in monodealkylation reactions.

Purpose of the Study:

  • To develop a more selective catalyst for ether cleavage.
  • To investigate the efficacy of non-pincer iridium complexes in C-O bond activation.
  • To explore the compatibility of this methodology with sensitive functional groups.

Main Methods:

  • Synthesis and testing of a simple, non-pincer iridium complex.
  • Evaluation of catalytic activity in the cleavage of benzylic ethers.
  • Assessment of selectivity in the presence of alkyl and aryl halides.
  • Preliminary mechanistic studies involving spectroscopic analysis.

Main Results:

  • The non-pincer iridium complex demonstrated improved selectivity in ether-to-silyl ether conversion.
  • Successful benzylic ether cleavage was achieved even with reductively-labile halide functionalities present.
  • Mechanistic studies indicated a neutral tetrahydridosilyliridium intermediate, aligning with prior hypotheses.
  • The pincer ligand framework was found to be non-essential for catalytic activity.

Conclusions:

  • Simple cationic bis(phosphine)iridium complexes are effective catalysts for ether cleavage.
  • These complexes offer enhanced selectivity compared to pincer-supported counterparts.
  • The findings pave the way for applying this method to more complex organic substrates.