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Nomenclature of Alkenes

Nomenclature of Alkenes

The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...

Isomerism in Alkenes

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...

Halogenation of Alkenes

Halogenation of Alkenes

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.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

EDTA: Auxiliary Complexing Reagents

EDTA: Auxiliary Complexing Reagents

EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.

Structure and Bonding of Alkenes

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...

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Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years.

Ji Hoon Lee¹, Sungwook Choi², Ki Bum Hong³

¹New Drug Development Center (NDDC), Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), 80 Cheombok-ro, Dong-gu, Daegu 701-310, Korea.

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|July 24, 2019

Summary

Hypervalent iodine reagents offer a powerful alternative to metal catalysts for organic synthesis. This review highlights recent advances in alkene functionalization using these versatile reagents.

Keywords:

alkene difunctionalization aminofunctionalization diacetoxylation diamination dihalogenation hypervalent iodine oxyfunctionalization

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Hypervalent iodine reagents offer a sustainable alternative to traditional transition metal catalysts.
Their applications have expanded significantly over the last two decades, including stoichiometric oxidation and catalytic asymmetric reactions.

Purpose of the Study:

To review the main advances in alkene heterofunctionalization using hypervalent iodine reagents over the past 10 years.
To cover both achiral and chiral hypervalent iodine reagents and catalysts.

Main Methods:

Literature review of recent advances in hypervalent iodine chemistry.
Focus on alkene heterofunctionalization reactions.

Main Results:

Significant progress in alkene heterofunctionalization using hypervalent iodine reagents.
Development of both achiral and chiral catalytic systems.
Demonstration of hypervalent iodine as a viable alternative to transition metals.

Conclusions:

Hypervalent iodine reagents are increasingly important in organic synthesis.
Recent advances have expanded their utility in alkene functionalization.
These reagents provide complementary strategies to transition metal catalysis.