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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

22.8K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
22.8K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.9K
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.
12.9K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.7K
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.
10.7K
Cycloalkanes02:28

Cycloalkanes

18.3K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
18.3K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.8K
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

15.0K
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...
15.0K

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Heteroatom-embedded medium-sized cycloalkynes: concise synthesis, structural analysis, and reactions.

Runyan Ni1, Naoto Mitsuda, Takeru Kashiwagi

  • 1Department of Molecular and Material Sciences, Kyushu University (Japan).

Angewandte Chemie (International Ed. in English)
|December 4, 2014
PubMed
Summary

Medium-sized cycloalkynes were synthesized using a double Nicholas reaction. These unique, reactive alkynes can be incorporated into peptides for new applications.

Keywords:
alkynescycloadditionheterocyclespeptidesstrained molecules

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Cycloalkynes are strained cyclic alkynes with unique reactivity.
  • The Nicholas reaction is a cobalt-mediated alkyne functionalization method.

Purpose of the Study:

  • To develop an efficient synthesis of medium-sized cycloalkynes.
  • To explore the reactivity of these novel cycloalkynes.
  • To incorporate cycloalkynes into peptide structures.

Main Methods:

  • Double Nicholas reaction utilizing cobalt complex and bis(hetero)substituted acyclic precursors.
  • Cycloaddition reactions to probe alkyne reactivity.
  • Peptide synthesis to embed cycloalkynes.

Main Results:

  • Efficient synthesis of various medium-sized cycloalkynes.
  • The synthesized cycloalkynes exhibit a bent structure and high reactivity.
  • Successful preparation of multifunctionalized alkynes via peptide incorporation.

Conclusions:

  • The double Nicholas reaction provides a viable route to medium-sized cycloalkynes.
  • The unique structural and reactive properties of these cycloalkynes open new avenues in synthetic chemistry.
  • Embedding cycloalkynes in peptides offers a novel strategy for creating complex biomolecules.