The Origins of Periselectivity and Substituent Effects in Electrocyclizations of o-Nitrosostyrenes: A Computational Study

Abstract

Density functional theory has been used to study four pericyclic, or pseudopericyclic, reactions that may be involved in the reductive transformation of o-nitrostyrenes to indoles. These are two electrocyclizations and two 1,5-hydride shifts. The reactions of substituted examples show computed relative barrier heights in agreement with experimental observations.

Key words

pericyclic reactions - indoles - electrocyclic reactions - rearrangements - substituent effects

References

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