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Tutorial MenuePericyclic ReactionsLearning Unit 6 of 6

Pericyclic Reactions: Further Examples

Pericyclic Reactions: Group Transfer Reactions

The reduction of double bonds with diimide is of synthetic value.

Reduction of alkenes with diimide

2D Animation of the reduction with diimide

The addition of H atoms from 1,4-cyclohexadiene to anthracene proceeds stereoselectively in cis fashion.

Reaction of anthracene with 1,4-cyclohexadiene

The driving force of the reaction is aromatization of cyclohexadiene to benzene. Loss of aromaticity in the middle ring of anthracene is less important because of the smaller stabilization energy of this ring as compared to benzene (see aromaticity).

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