What Are Diels-Alder Reaction?

Decent Essays
The Diels-Alder reaction (DA) is a [4+2] cycloaddition reaction of conjugated diene and dienophile. Since its discovery1, it has been recognized one of the keystone methods in organic synthesis for the formation of six membered rings.2 It has break new ground in the construction of many complex organic molecules.3 Fig. 1
The utility of the DA reaction has been further expanded by the incorporation of heteroatoms in both the diene and dienophile and are known as hetero-Diels-Alder (HDA) reaction.4
The HDA reaction is one of the most used synthetic strategies for the construction of six membered heterocyclic compounds5 having specific nature for example drugs or natural products.6
Various heteroatoms are capable HDA reaction, the most common being oxygen, nitrogen and sulphur. Here the emphasis will be on oxa-cycloaddition reaction.
…show more content…
dihydropyran accessible, which occurs as structural pattern in many biologically active natural products.7
Hetero-Diels-Alder reactions of carbonyl compound can be classified into two types of [π2s+ π4s] cycloadditions, the normal and inverse electron demand cycloadditions (Fig. 2) based on the relative frontier molecular orbitals (FMOs) energies of diene and

Related Documents

  • Improved Essays

    In Experiment 12B we used an umpolung reagent in an umpolung synthesis to synthesize benzoin from benzaldehyde. Umpolung synthesis is a synthetic approach that allows us to switch the identity of a reacting species. For example, the normal chemical reactivity of a nucleophile can be switched to one of an electrophilic compound. Two common agents are cyanide and thiamine (Vitamin B). The mechanisms for both agents are the same.…

    • 484 Words
    • 2 Pages
    Improved Essays
  • Improved Essays

    In this experiment, the phosphonium salt used was benzyltriphenylphosphonium chloride, which was provided by the instructor. During synthesis of the phosphonium salt, the ylide was formed in the presence of the phenyl group. The phenyl group provides stabilization. The cinnamaldehyde then reacts with the ylide to form a product of 1,4-diphenyl-1,3-butadiene. The ylide-forming reaction occurs in a set of two phases.…

    • 858 Words
    • 4 Pages
    Improved Essays
  • Decent Essays

    Stereochemistry 5. Introduction In this experiment, stereochemistry was explored by the isomerization of dimethyl maleate and the analysis of carvones. The isomerization was accomplished with the use of bromine, which broke the double bond to allow bond rotation. Free bond rotation allowed molecules to shift into the trans state before the double bond was reformed to create dimethyl fumarate.…

    • 929 Words
    • 4 Pages
    Decent Essays
  • Superior Essays

    (4) Scheme 4. The third possible product when 2-ethyl-1,3-hexanediol undergoes oxidation reaction.…

    • 1586 Words
    • 7 Pages
    Superior Essays
  • Improved Essays

    The appearance of strong OH bonds, C= O bonds, and sp3 CH3 bonds in the infrared spectrum of the final product showed the presence of the desired product (4-t-butylcyclohexanol ). However, the reaction did not go to full completion because the IR showed that the starting material was still present by the peak at 1710.61 of the ketone C=O bonds. From this experiment, it was found that it is import to follow the steps carefully in order to have a complete completion of the…

    • 552 Words
    • 3 Pages
    Improved Essays
  • Decent Essays

    Dehydrobromination of meso-Stilbene Dibromide Introduction This procedure was performed in order to synthesize an alkyne from meso-stilbene dibromide through double dehydrohalogenation. The removal of the two bromine and two hydrogen atoms allows for the formation of the carbon triple bond and thus the formation of an alkyne. The alkyne formed is diphenylacetylene.…

    • 534 Words
    • 3 Pages
    Decent Essays
  • Improved Essays

    Green Chemistry and the Diels-Alder Reaction Purpose The purpose of this reaction is to bring about the movement of green chemistry which is a safer, more sustainable chemistry to all levels of chemistry. The use of 12 principles can make in principle a reaction greener with the use of modifications. In this lab, the Diels-Alder reaction will be performed by reacting (E,E)-2,4-hexadien-1-ol with maleic anhydride without the use of a solvent to make the reaction more greener.…

    • 745 Words
    • 3 Pages
    Improved Essays
  • Improved Essays

    This the reaction involves a tertiary alkyl halide, which is tert-butyl chloride, which further indicates that the reaction follows a SN1…

    • 1172 Words
    • 5 Pages
    Improved Essays
  • Great Essays

    Examination and Exercise of Green Chemistry through the Cyclohexanol Cycle Jesse Paner CHE 233L Section 301 Department of Chemistry, DePaul University, 1110 W. Belden Avenue, Chicago, IL 60614 panerjesse@yahoo.com May 1st, 2017 Abstract Green chemistry emphasizes the utilization of chemicals to their highest efficiency and reducing the production of harmful waste. This type of chemistry was initially conceived in order to reduce the damaging impact that chemical products have on the environment. Through a series of experiments known as the cyclohexanol cycle, green chemistry was observed.…

    • 1109 Words
    • 5 Pages
    Great Essays
  • Decent Essays

    Anthracene Formal Report

    • 122 Words
    • 1 Pages

    The purpose of this experiment was to synthesize 9,10-dihydroanthracene-9,10-α,β- succinic anhydride by performing a Diels-Alder reaction of anthracene with maleic anhydride. This reaction can also be called a cycloaddition, because the diene, anthracene, is added to the an alkene, maleic anhydride, to produce a cyclic compound. Since anthracene is a cyclic diene, it also favors an endo product despite sterical hindrance. The Diels-Alder reaction is a very powerful reaction and useful in synthetic organic chemistry due to its good control over regio- and stereochemical properties.…

    • 122 Words
    • 1 Pages
    Decent Essays
  • Great Essays

    Ethyl Cinnamate Synthesis

    • 921 Words
    • 4 Pages

    Experiment 5 Synthesis and NMR Spectroscopy of ethyl cinnamate Introduction: Wittig reactions involve the stereoselective synthesis of olefins from phosphonium ylides and aldehydes or ketones, where the carbonyl bond is converted to an alkene double bond.1 The variety of suitable reagents and the relatively mild experimental conditions facilitate their industrial applications, such as the synthesis of epoxides, esters, carotenoids and vitamin A.2,3 Specifically, the ester ethyl cinnamate is used as a flavouring agent and in perfumes. The diastereomers of the alkene are distinguished through Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, where the coupling constants of alkenyl protons are different for (E) and (Z) isomers.4…

    • 921 Words
    • 4 Pages
    Great Essays
  • Decent Essays

    The Aldol Reaction Lab

    • 279 Words
    • 2 Pages

    Solventless Reactions: The Aldol Reaction CH204-01 Fadwa Mekkaoui Introduction: An aldol reaction is the formation of a new carbon-carbon bond by the addition of a nucleophile to an electron deficient carbon. The reaction is favorable in Green Chemistry. It demonstrates green principles such as using no solvent and having a high atom economy.…

    • 279 Words
    • 2 Pages
    Decent Essays
  • Great Essays

    Nucleophilic substitutions are a fundamental class of reactions in organic chemistry. This type of reaction involves a nucleophile, or an electron rich species, attacking an electrophilic site, or an area that carries a positive or partially positive charge, in order to replace a leaving group. There are two possible mechanisms to account for the attack of the nucleophile; the first occurs in a concerted process, or in one step and the second mechanism occurs in two steps and involves a carbocation intermediate. As the nucleophile is attacking in the concerted process, the leaving group is leaving, thus the atom does not break the octet rule. This type of reaction, known as an SN2 reaction, has a rate that is dependent on both the concentration of the substrate in addition to the concentration of the nucleophile.…

    • 1561 Words
    • 7 Pages
    Great Essays
  • Decent Essays

    1)Macro-social storytelling agents include institutions or organizations having storytelling production and dissemination resources such as large media, political, religious and other media. For instance, agencies or corporations with public information or relations capacities can be viewed as macro-social storytelling agents.[P431] 2) Intermediate/Meso-social storytelling agents are smaller and more locally based organizations, including community media and community organizations targeted to residents, whose primary goals are to create linkage in a particular residential area. 3) Micro-social storytelling agents are interpersonal networks…

    • 79 Words
    • 1 Pages
    Decent Essays
  • Improved Essays

    Paracetamol Lab Report

    • 651 Words
    • 3 Pages

    These two steps were already carried out and 4 amino-phenol was the amine used in the first part of this experiment. 4 amino phenol and acetic anhydride undergo a nucleophilic addition-elimination reaction. A reaction mechanism is a step-by-step process when reactant molecules change in their geometry in order to produce new products. This occurs due to omission or addition of reagents, where bonds are broken down to form new ones4. 4 amino-phenol contains two functional groups, an OH and a NH2 group attached to a benzene ring while acetic anhydride is a derivative of a carboxylic acid group.…

    • 651 Words
    • 3 Pages
    Improved Essays