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Updated: Jan 6, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Epoxidation of Alkenes by Peracids: From Textbook Mechanisms to a Quantum Mechanically Derived Curly-Arrow Depiction
Johannes E M N Klein1, Gerald Knizia2, Henry S Rzepa3
1Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, Faculty of Science and Engineering University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands.
Abstract:
Using the intrinsic bond orbital (IBO) analysis based on accurate quantum mechanical calculations of the reaction path for the epoxidation of propene using peroxyacetic acid, we find that the four commonly used curly arrows for representing this reaction mechanism are insufficient and that seven curly arrows are required as a result of changes to σ and π bonding interactions, which are usually neglected in all textbook curly arrow representations. The IBO method provides a convenient quantitative method for deriving curly arrows in a rational manner rather than the normal ad hoc representations used ubiquitously in teaching organic chemistry.
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