ArticleThe Journal of organic chemistry2024
A 21st Century View of Allowed and Forbidden Electrocyclic Reactions.
Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
10 citing papers in PubMed, 22 citations in OpenAlex.
- Programmable regiodivergent light-driven cyclization of acyclic 1,5-dienes unlocks rigid bicyclic architectures.Nature chemistry · 2026Article
- Stereoselective Higher-Order [10+4]- and [10+6] Cycloadditions Between Two Highly Unsaturated and Ambiphilic π-Addends.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Creating a Masterpiece. The Road to (and Beyond) Woodward and Hoffmann's 1969 Angewandte Chemie Treatise.Chemical record (New York, N.Y.) · 2026Review
- Vitamin D in Photosynthetic Organisms and Fungi: Sterol Photochemistry, UV-B Availability, and Biofortification Potential.Current issues in molecular biology · 2026Review
- Computational Study of Ignored Pericyclic Reactions: Rearrangements of 1,2-Bis(Diazo)Alkanes to 1,2,3,4-Tetrazines and Subsequent Fragmentations.Angewandte Chemie (International ed. in English) · 2025Article
- Woodward and Hoffmann on Secondary Orbital Interactions. How to Make a Fine Two-Course Meal from Leftovers.Chemical record (New York, N.Y.) · 2025Review
- Self-Sensitized Fulgimides with Selective Multiplicity-Based Three-State Photoswitching.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- The fellowship of the Grignard: 21st century computational tools for hundred-year-old chemistry.Chemical science · 2025Review
- Converting Second-Order Saddle Points to Transition States: New Principles for the Design of 4π Photoswitches.Chemphyschem : a European journal of chemical physics and physical chemistry · 2025Article
- Going Beyond Woodward and Hoffmann's Electrocyclizations and Cycloadditions: Sigmatropic Rearrangements.Chemical record (New York, N.Y.) · 2024Review
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In 1965, Woodward and Hoffmann proposed a theory to predict the stereochemistry of electrocyclic reactions, which, after expansion and generalization, became known as the Woodward-Hoffmann Rules. Subsequently, Longuet-Higgins and Abrahamson used correlation diagrams to propose that the stereoselectivity of electrocyclizations could be explained by the correlation of reactant and product orbitals with the same symmetry. Immediately thereafter, Hoffmann and Woodward applied correlation diagrams to explain the mechanism of cycloadditions. We describe these discoveries and their evolution. We now report an investigation of various electrocyclic reactions using DFT and CASSCF. We track the frontier molecular orbitals along the intrinsic reaction coordinate and modeled trajectories and examine the correlation between HOMO and LUMO for thermally forbidden systems. We also investigate the electrocyclizations of several highly polarized systems for which the Houk group had predicted that donor-acceptor substitution can induce zwitterionic character, thereby providing low-energy pathways for formally forbidden reactions. We conclude with perspectives on the field of pericyclic reactions, including a refinement as the meaning of Woodward and Hoffmann's "Violations. There are none!" Lastly, we comment on the burgeoning influence of computations on all fields of chemistry.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.