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Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Structure and Physical Properties of Alkynes

Structure and Physical Properties of Alkynes

Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Gold(III) Alkyne Complexes: Bonding and Reaction Pathways.

Luca Rocchigiani¹, Julio Fernandez-Cestau¹, Gabriele Agonigi¹

¹School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK.

Angewandte Chemie (International Ed. in English)

|September 12, 2017

Summary

Researchers synthesized and characterized novel gold(III) π-alkyne complexes, revealing key factors influencing their stability and reactivity compared to platinum(II) complexes. This work opens new avenues in gold-mediated carbon-carbon bond formation.

Keywords:

alkynes density functional calculations gold homogeneous catalysis reaction mechanisms

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Area of Science:

Organometallic Chemistry
Gold Chemistry
Alkyne Coordination

Background:

Classical platinum(II) alkyne complexes are well-studied.
Hypothetical gold(III) π-alkyne complexes present unique bonding and reactivity challenges.

Purpose of the Study:

To synthesize and characterize novel gold(III) π-alkyne complexes.
To elucidate the factors governing their stability and reactivity.
To compare their behavior with platinum(II) alkyne complexes.

Main Methods:

Synthesis of gold(III) π-alkyne complexes.
Characterization using spectroscopic and analytical techniques.
Computational studies on bonding and stability.

Main Results:

Successful synthesis and characterization of hypothetical gold(III) π-alkyne complexes.
Stability and bonding are strongly influenced by trans effect and steric factors.
Lack of back-bonding in gold(III) complexes facilitates alkyne slippage compared to platinum(II).

Conclusions:

Gold(III) complexes are significantly more reactive than platinum(II) congeners due to electronic and steric effects.
The propensity of gold to facilitate C-C bond formation is explained by energetic favorability of alkyne slippage.
A new reaction sequence involving cycloaddition, aryl migration, and reductive deprotonation in gold chemistry was demonstrated.