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Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

2.4K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

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Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
14.5K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.2K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

5.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.0K
Reactivity of Enols01:18

Reactivity of Enols

3.4K
Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
3.4K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.5K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.5K

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

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Reactivity of hydroxy- and aquo(hydroxy)-λ3-iodane-crown ether complexes.

Kazunori Miyamoto1, Yukie Yokota, Takashi Suefuji

  • 1Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505 (Japan). kmiya@tokushima-u.ac.jp.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 20, 2014
PubMed
Summary

New shelf-stable hydroxy(aryl)-λ(3)-iodane-[18]crown-6 complexes offer potent oxidation capabilities in water. These reagents efficiently oxidize various organic compounds and serve as precursors for synthesizing diverse iodanes in aqueous media.

Keywords:
crown ethershypervalent compoundsiodineoxidationsupramolecules

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Hypervalent iodine compounds are versatile oxidants.
  • Developing stable and water-compatible hypervalent iodine reagents remains a challenge.

Purpose of the Study:

  • To design and synthesize novel hydroxy(aryl)-λ(3)-iodane-[18]crown-6 complexes.
  • To investigate their reactivity and utility in aqueous media for oxidation reactions and iodane synthesis.

Main Methods:

  • Synthesis of hydroxy(aryl)-λ(3)-iodane-[18]crown-6 complexes from iodosylbenzene derivatives and superacids with [18]crown-6.
  • Evaluation of reagent stability, shelf-storage, and oxidizing ability in water.
  • Testing reactivity towards phenols, sulfides, olefins, silyl enol ethers, and alkyl(trifluoro)borates.
  • Assessing the complexes as progenitors for diaryl-, vinyl-, and alkynyl-λ(3)-iodane synthesis.

Main Results:

  • The designed complexes are non-hygroscopic and shelf-storable.
  • They exhibit high oxidizing ability in aqueous media under mild conditions.
  • Effective oxidation of a range of organic substrates was achieved.
  • The complexes successfully served as precursors for synthesizing various iodanes in water.

Conclusions:

  • Hydroxy(aryl)-λ(3)-iodane-[18]crown-6 complexes represent stable, water-compatible hypervalent iodine reagents.
  • These complexes offer a green and efficient platform for oxidation and iodane synthesis in aqueous environments.
  • The methodology is applicable in various organic solvents, enhancing its versatility.