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Corey–Chaykovsky epoxidation template
Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of MolDraw Pro.
Trimethylsulfonium is deprotonated to the ylide, which adds to cyclohexanone; the alkoxide displaces Me₂S to form the spiro-epoxide.
Mechanism step by step
A sulfur ylide adds to C=O and closes to an epoxide (not an alkene)
- Ylide – tert-Butoxide removes a C–H next to S⁺
- Addition – The ylide carbon attacks C=O: a betaine
- Ring closure – The alkoxide displaces Me₂S (intramolecular SN2)
Key points
- Compare the Wittig: there P=O forms, here the weaker S–O bond does not, so the oxygen stays and closes the ring.
- Dimethylsulfoxonium methylide (Me₂S(O)=CH₂) gives cyclopropanes with enones.
- Methylene transfer to aldehydes, ketones and imines (giving aziridines).
- Me₂S leaves as a neutral molecule: a very good leaving group.
Drawn with 81 atoms, 10 arrows, 5 shapes – every one editable in MolDraw.
Sources
How to use this template
- Press Edit in MolDraw. The template opens on the canvas of the free MolDraw editor.
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Frequently asked questions
Is the Corey–Chaykovsky epoxidation template free?
You can preview the Corey–Chaykovsky epoxidation 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 Corey–Chaykovsky epoxidation 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.
Which name reactions are included?
Over seventy, covering the reactions most often asked in school-leaving exams (A-level, IB, CBSE, JEE and NEET) and first-year university courses, including condensations, rearrangements, oxidations, reductions and aromatic substitutions.