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Pericyclic Reactions Lecture Notes

This document discusses pericyclic reactions, which proceed in a single concerted step via the formation of a cyclic transition state involving π or σ electrons. Pericyclic reactions are classified into three categories: cycloaddition reactions, electrocyclic reactions, and sigmatropic rearrangements. Cycloaddition reactions involve the combination of two molecules to form a ring by converting two π-bonds into two sigma bonds. Electrocyclic reactions involve a reversible cyclization of a compound with conjugated double bonds, using two π-electrons to form a σ-bond. Sigmatropic rearrangements are concerted intramolecular rearrangements where an atom or group shifts positions, breaking one bond and forming a new one.

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3K views2 pages

Pericyclic Reactions Lecture Notes

This document discusses pericyclic reactions, which proceed in a single concerted step via the formation of a cyclic transition state involving π or σ electrons. Pericyclic reactions are classified into three categories: cycloaddition reactions, electrocyclic reactions, and sigmatropic rearrangements. Cycloaddition reactions involve the combination of two molecules to form a ring by converting two π-bonds into two sigma bonds. Electrocyclic reactions involve a reversible cyclization of a compound with conjugated double bonds, using two π-electrons to form a σ-bond. Sigmatropic rearrangements are concerted intramolecular rearrangements where an atom or group shifts positions, breaking one bond and forming a new one.

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Dept. of Chemistry, Sri Sarada Niketan, Kanavaipudur.

UNIT 4

Pericyclic Reactions

1. Most of the organic reactions proceed in a stepwise manner. However, there are certain
reactions, which proceed in a single concerted step via the formation of a cyclic transition
state involving п or σ electrons. Such reactions are called pericyclic reactions.
2. The energy for pericyclic reactions is supplied by heat in a thermally induced reaction or
by ultraviolet light in a photo-induced reaction.
3. Pericyclic reactions are highly stereospecific.
4. Pericyclic reactions do not involve ionic or free radical intermediates and so solvents and
reagents have no effect on the course of the reaction.

Classification of Pericyclic reactions

Generally pericyclic reactions are classified into the following three categories:

1. Cycloaddition reactions
2. Electrocyclic reactions
3. Sigmatropic rearrangements

1. Cycloaddition reactions

In these reactions, two molecules combine to form a ring. The reaction involves conversion
of two п-bonds into two sigma bonds. An example of cycloaddition reaction is the well-known
Diels-Alder reaction.

2. Electrocyclic reactions

These are reversible reactions in which a compound with conjugated double bonds
undergoes cyclization. In this process two п-electrons are used to form a σ-bond. Thus, 1,3,5-
hexatriene on heating gives 1,3-cyclohexadiene.

Page 1 of 2
Dept. of Chemistry, Sri Sarada Niketan, Kanavaipudur.

In the above illustration, an electrocyclic ring closure takes place. The reverse of this
process is an electrocyclic ring opening.

3. Sigmatropic rearrangements

These are concerted intramolecular rearrangements. In these rearrangements, an atom or a


group of atoms shifts from one position to another. The process involves breaking of a bond and
formation of a new bond. Thus, 3-methyl-1,5-hexadiene on heating gives 1,5-heptadiene.

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