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Cycloaddition Reactions

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Essentials of Pericyclic and Photochemical Reactions

Part of the book series: Lecture Notes in Chemistry ((LNC,volume 93))

Abstract

Cycloaddition reactions are the most useful pericyclic reactions in organic synthesis. These reactions are characterized by joining two π systems at their ends to form a ring compound through the formation of two new sigma bonds via the breaking of two π bonds, one from each π system in a concerted process. These reactions are classified according to the number of π electrons involved in each reacting component. The major classes are [π2+π2]-, [π4+π2]-, [π6+π2]-, [π8+π2]- and [π6+π4]-cycloaddition reactions. These are simply known as [2+2]-, [4+2]-, [6+2]-, [8+2]- and [6+4]-cycloaddition reactions. Among them, the Diels–Alder reactions and 1,3-dipolar cycloaddition reactions are widely applied in the synthesis of different types of polycyclic and heterocyclic compounds. Both these reactions are highly regio- and stereoselective and produce syn-addition products. Cheletropic reactions are a special group of cycloaddition or cycloreversion reactions, in which two sigma bonds are made or broken in the same atom of an electrophilic reacting component. The regio-, stereo- and enantioselectivities of the major classes of cycloaddition reactions and their wide applications in the synthesis of different classes of organic compounds have been discussed.

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  1. Department of Chemistry, Tripura University, Agartala, Tripura, India

    Biswanath Dinda

  2. Department of Chemistry, NIT Agartala, Jirania, India

    Biswanath Dinda

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Dinda, B. (2017). Cycloaddition Reactions. In: Essentials of Pericyclic and Photochemical Reactions. Lecture Notes in Chemistry, vol 93. Springer, Cham. https://doi.org/10.1007/978-3-319-45934-9_3

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