In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally-allowed [4+2] cycloaddition with Woodward–Hoffmann symbol [π4s + π2s]. It was first described by Otto Diels and Kurt Alder in 1928. For the discovery of this reaction, they were awarded the Nobel Prize in Chemistry in 1950. Through the simultaneous construction of two new carbon–carbon bonds, the Diels–Alder reaction provides a reliable way to form six-membered rings with good control over the regio- and stereochemical outcomes. Consequently, it has served as a powerful and widely applied tool for the introduction of chemical complexity in the synthesis of natural products and new materials. The underlying concept has also been applied to π-systems involving heteroatoms, such as carbonyls and imines, which furnish the corresponding heterocycles; this variant is known as the hetero-Diels–Alder reaction. The reaction has also been generalized to other ring sizes, although none of these generalizations have matched the formation of six-membered rings in terms of scope or versatility. Because of the negative values of ΔH° and ΔS° for a typical Diels–Alder reaction, the microscopic reverse of a Diels–Alder reaction becomes favorable at high temperatures, although this is of synthetic importance for only a limited range of Diels-Alder adducts, generally with some special structural features; this reverse reaction is known as the retro-Diels–Alder reaction.
The reaction is an example of a concerted pericyclic reaction. It is believed to occur via a single, cyclic transition state, with no intermediates generated during the course of the reaction.
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To develop basic understanding of the reactivity of aromatic and heteroaromatic compounds. To develop a knowledge of a class of pericyclic reactions. To apply them in the context of the synthesis.
The development of an unusual oxidative alkene difunctionalization using methyl formate and syn-thetic studies towards alkaloid natural products provide the basis of the thesis. The first chapter deta
EPFL2020
Current thesis summarizes the work on development of novel bioluminescent probes for measurement of activity of dipeptidylpep-tidase-4 (DPP-4) and for quantification of mitochondrial membrane potentia
EPFL2018
Triazenes have garnered great attention for their anti-cancer properties and versatility in organic chemistry. Recently, a novel synthesis of 1-alkynyl triazenes was reported. This thesis describes th