--- title: "Claisen rearrangement Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/pericyclic-claisen/ description: "Claisen rearrangement template: Allyl vinyl ether rearranges to pent-4-enal; allyl phenyl ether gives a cyclohexadienone that tautomerises to 2-allylphenol.…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-reactions/) › Claisen rearrangement [Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-reactions/)Premium # Claisen rearrangement template ![Claisen rearrangement template: Allyl vinyl ether rearranges to pent-4-enal; allyl phenyl ether gives a cyclohexadienone that tautomerises to 2-allylphenol.](https://www.moldraw.com/templates/pericyclic-claisen.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). Allyl vinyl ether rearranges to pent-4-enal; allyl phenyl ether gives a cyclohexadienone that tautomerises to 2-allylphenol. ## Mechanism step by step A [3,3]-sigmatropic shift of an allyl vinyl or allyl aryl ether to a C=O compound 1. **Aliphatic Claisen** – The C–O σ bond breaks as C–C forms: a chair of six atoms 2. **Aromatic Claisen** – The allyl group moves to the ortho carbon (inverted: C3 of the allyl bonds) 3. **Tautomerisation** – Loss of the ring C–H restores the aromatic ring: 2-allylphenol ## Key points - Concerted and suprafacial [3,3] shift: six electrons, thermally allowed, chair-like transition state. - Making a strong C=O bond (and losing C–O) makes the aliphatic version irreversible and exothermic. - Stereospecific: E or Z allyl ethers give different diastereomers, and a stereocentre on the allyl chain is transferred to the new C–C bond. - Variants: Ireland–Claisen (silyl ketene acetals), Johnson–Claisen (orthoesters), Eschenmoser–Claisen (amide acetals). Drawn with 67 atoms, 13 arrows, 5 shapes – every one editable in MolDraw. ## Sources - [Woodward & Hoffmann, Angew. Chem. Int. Ed. Engl. 1969, 8, 781](https://doi.org/10.1002/anie.196907811) Review - [Fleming, Molecular Orbitals and Organic Chemical Reactions, Wiley 2010](https://openlibrary.org/isbn/9780470746585) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 35](https://openlibrary.org/isbn/9780199270293) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Claisen rearrangement template free? You can preview the Claisen rearrangement template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Claisen rearrangement template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### Do the pericyclic templates show orbital symmetry? They show the curly arrows, the stereochemical outcome and the Woodward–Hoffmann rule that predicts it (conrotatory or disrotatory, endo or exo). ## More pericyclic reactions templates [**Diels–Alder reaction: the endo rule**Free · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-diels-alder-endo/)[**Diels–Alder regiochemistry**Free · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-diels-alder-regio/)[**Cope and oxy-Cope rearrangements**Free · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-cope-oxy-cope/)[**Electrocyclic ring closure**Premium · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-electrocyclic/)[**1,3-Dipolar cycloaddition**Premium · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-dipolar-cycloaddition/) ## Related pages [**Curved Arrow Mechanism Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/curved-arrow-mechanism-worksheet/)[**All Pericyclic reactions templates**6 templates](https://www.moldraw.com/templates/pericyclic-reactions/)[**All chemistry templates**370 templates in 29 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 370 templates - Export the 291 premium templates as PNG, SVG or PDF - AI chemistry assistant - Structure scanning from images - Cloud save and teaching slides [See Pro plans](https://www.moldraw.com/pricing) Free templates stay free. 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