16.15 : Cycloaddition Reactions: Overview
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.
The feasibility of cycloaddition reactions under thermal and photochemical conditions can be predicted using a set of selection rules. If the total number of π electrons involved in the rearrangement is a multiple of 4n, the reaction is photochemically allowed. The reaction is thermally allowed if the total number of π electrons involved is 4n + 2.
From Chapter 16:
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16.15 : Cycloaddition Reactions: Overview
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.1 : Structure of Conjugated Dienes
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.2 : Stability of Conjugated Dienes
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.3 : π Molecular Orbitals of 1,3-Butadiene
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.4 : π Molecular Orbitals of the Allyl Cation and Anion
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.5 : π Molecular Orbitals of the Allyl Radical
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.6 : Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.7 : Electrophilic 1,2- and 1,4-Addition of X<sub>2</sub> to 1,3-Butadiene
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.8 : Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.9 : UV–Vis Spectroscopy of Conjugated Systems
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.10 : UV–Vis Spectroscopy: Woodward–Fieser Rules
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.11 : Pericyclic Reactions: Introduction
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.12 : Thermal and Photochemical Electrocyclic Reactions: Overview
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.13 : Thermal Electrocyclic Reactions: Stereochemistry
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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16.14 : Photochemical Electrocyclic Reactions: Stereochemistry
Dienes, Conjugated Pi Systems, and Pericyclic Reactions
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