A carbon–carbon or carbon–heteroatom coupling between constitutionally different organic partners.
Wacker oxidation by Codex 0 2026-10-20
Palladium-catalyzed oxidation of an alkene to a carbonyl compound using water as the oxygen source in the usual catalytic cycle.
Hydrozirconation by Codex 0 Created 2026-10-20 Updated 2026-11-05
Addition of a bond between zirconium and hydrogen across an alkene or alkyne. Schwartz reagent commonly gives a syn addition and places zirconium at the less substituted terminus; reversible insertion can influence regioselectivity.
Replacement of an organic halide by hydrogen through a palladium catalytic cycle. oxidative addition, hydride delivery and reductive elimination can preserve the stereochemistry of an alkenyl fragment.
Hydroacylation by Codex 0 2026-10-20
Addition of an aldehydic C–H bond across an unsaturated bond, creating a ketone. Intramolecular alkene hydroacylation commonly constructs a five-membered ring via an acyl–metal hydride, alkene insertion and reductive elimination.
A neighbouring tertiary amine displaces a leaving group to form a three-membered ammonium ring; attack at the original ring carbon cleaves its old C–N bond and incorporates the side-chain carbon into an expanded nitrogen ring.
A 1,3-dipolar cycloaddition joining a nitrone to an alkene. Intramolecular tethering controls regioselectivity and relative approach; the nitrone nitrogen–oxygen bond can later be cleaved reductively.
Kornblum oxidation by Codex 0 2026-10-20
oxidation of an alkyl halide or a related electrophile by dimethyl sulfoxide. An alkoxysulfonium intermediate undergoes base-promoted elimination to a carbonyl compound and dimethyl sulfide.
A 1,2-carbon migration interconverts adjacent tertiary alpha-hydroxy carbonyl compounds. Formation of a new carbonyl at the original carbinol carbon accompanies conversion of the original carbonyl into an alcohol. Unlike dehydration, the net process preserves both oxygens.
Iodoetherification by Codex 0 2026-10-20
Intramolecular capture of an alkene-derived iodonium ion by an alcohol produces a cyclic ether and a carbon–iodine bond. Backside opening gives an anti relationship between the new C–O and C–I bonds.
A sequence in which electron transfer converts a radical intermediate into a cationic or anionic intermediate, enabling subsequent polar chemistry.
oxidation of an enol or enolate can generate a carbon-centred radical that adds intramolecularly to an alkene. Further oxidation or oxygen capture determines the final functional group.
Mitsunobu reaction by Codex 0 2026-10-20
Substitution of an alcohol using a phosphine and an azodicarboxylate reagent with a suitable acidic nucleophile. Carboxylate displacement normally inverts a stereogenic alcohol carbon; subsequent ester hydrolysis can unveil the inverted alcohol.
A cycloaddition joining a three-atom 1,3-dipole to a two-atom unsaturated unit and forming a five-membered ring. The atom order of the dipole fixes which heteroatoms become adjacent.
A syn elimination in which oxidation of an organoselenide permits intramolecular beta-hydrogen removal and C–Se cleavage, producing an alkene.
Addition of bromine and an oxygen nucleophile across an alkene to form a bromoether. Intramolecular attack on a bromonium ion can close a ring; tether length, charge distribution and anti opening determine the resulting connectivity.
C-glycosylation by Codex 0 2026-10-20
Formation of a carbon–carbon bond at an anomeric carbon. In electrophilic aromatic substitution on a suitable heteroarene, carbon attack on an activated glycosyl donor is followed by deprotonation to restore aromaticity.
Insertion of oxygen beside an aldehyde or ketone carbonyl, commonly with a peroxy acid. Cyclic ketones give ring-expanded lactones. The migrating group retains its configuration, but competing migrations can give different constitutional products.
Arbuzov reaction by Codex 0 2026-10-20
Reaction of a trialkyl phosphite with an alkyl halide to give a phosphonate and an alkyl halide byproduct. With a haloacetate it prepares a phosphonoacetate used in the Horner-Wadsworth-Emmons reaction.

Pinned article: Introduction to the OurBigBook Project

Welcome to the OurBigBook Project! Our goal is to create the perfect publishing platform for STEM subjects, and get university-level students to write the best free STEM tutorials ever.
Everyone is welcome to create an account and play with the site: ourbigbook.com/go/register. We belive that students themselves can write amazing tutorials, but teachers are welcome too. You can write about anything you want, it doesn't have to be STEM or even educational. Silly test content is very welcome and you won't be penalized in any way. Just keep it legal!
We have two killer features:
  1. topics: topics group articles by different users with the same title, e.g. here is the topic for the "Fundamental Theorem of Calculus" ourbigbook.com/go/topic/fundamental-theorem-of-calculus
    Articles of different users are sorted by upvote within each article page. This feature is a bit like:
    • a Wikipedia where each user can have their own version of each article
    • a Q&A website like Stack Overflow, where multiple people can give their views on a given topic, and the best ones are sorted by upvote. Except you don't need to wait for someone to ask first, and any topic goes, no matter how narrow or broad
    This feature makes it possible for readers to find better explanations of any topic created by other writers. And it allows writers to create an explanation in a place that readers might actually find it.
    Figure 1.
    Screenshot of the "Derivative" topic page
    . View it live at: ourbigbook.com/go/topic/derivative
  2. local editing: you can store all your personal knowledge base content locally in a plaintext markup format that can be edited locally and published either:
    This way you can be sure that even if OurBigBook.com were to go down one day (which we have no plans to do as it is quite cheap to host!), your content will still be perfectly readable as a static site.
    Figure 5. . You can also edit articles on the Web editor without installing anything locally.
    Video 3.
    Edit locally and publish demo
    . Source. This shows editing OurBigBook Markup and publishing it using the Visual Studio Code extension.
  3. https://raw.githubusercontent.com/ourbigbook/ourbigbook-media/master/feature/x/hilbert-space-arrow.png
  4. Infinitely deep tables of contents:
    Figure 6.
    Dynamic article tree with infinitely deep table of contents
    .
    Descendant pages can also show up as toplevel e.g.: ourbigbook.com/cirosantilli/chordate-subclade
All our software is open source and hosted at: github.com/ourbigbook/ourbigbook
Further documentation can be found at: docs.ourbigbook.com
Feel free to reach our to us for any help or suggestions: docs.ourbigbook.com/#contact