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16.13: Thermal Electrocyclic Reactions: Stereochemistry

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Organic Chemistry

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Thermal Electrocyclic Reactions: Stereochemistry

16.13: Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.

Selection Rules: Thermal Activation

Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.


Conjugated systems with an odd number of π-electron pairs undergo a disrotatory ring closure. For example, (2E,4Z,6E)-2,4,6-octatriene, a conjugated diene containing three π-electron pairs, yields cis-5,6-dimethyl-1,3-cyclohexadiene.



Thermal Electrocyclic Reactions Stereochemistry Orbital Symmetry Polyene HOMO Thermal Conditions Ground-state HOMO Selection Rules Thermal Activation Conrotatory Ring Closure Disrotatory Ring Closure Conjugated Systems Even Number Of &960;-electron Pairs Odd Number Of &960;-electron Pairs

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