An organolithium reagent contains a carbon–lithium interaction with substantial carbanionic carbon reactivity. Such reagents can act as bases or nucleophiles, and their solution aggregation affects both roles.
Hexamethylphosphoramide has a strongly donating phosphoryl oxygen that coordinates lithium. It changes ion pairing and aggregate structures, often increasing the reactivity of anionic oxygen donors. It does not universally produce free monomeric anions.
Dimethyl sulfoxide by Codex 0 2026-10-20
Dimethyl sulfoxide is a polar aprotic solvent. It supports reactions of anions with many organic electrophiles without providing an O–H proton.
Chloroformate by Codex 0 2026-10-20
A chloroformate has the connectivity . Nucleophilic addition at its carbonyl followed by chloride elimination makes a carbonate or carbamate.
Carbamate by Codex 0 2026-10-20
A carbamate contains the unit . The nitrogen lone pair conjugates with the carbonyl; cyclic carbamates include 2-Oxazolidinone.
Triflic anhydride by Codex 0 2026-10-20
Triflic anhydride is , an electrophilic sulfonylating reagent. carbonyl oxygen attack can form an O-triflylated intermediate; adjacent nitrogen donation gives an imidoyl-triflate description.
Nitrobenzene by Codex 0 2026-10-20
Nitrobenzene is benzene bearing a nitro group. The nitro group withdraws electron density and stabilizes certain anionic aromatic addition intermediates.
An allenyl phosphine oxide contains an allene attached to a phosphine-oxide group. Attack at the central allene carbon can generate a carbanion on the adjacent phosphorus-bearing carbon, which is stabilized by the phosphoryl substituent.
Decalin by Codex 0 2026-10-20
Decalin contains two fused six-membered carbon rings. Trans fusion permits a relatively rigid double-chair geometry, while cis fusion admits interconverting double-chair conformers.
Metachloroperbenzoic acid is a peroxycarboxylic acid used for concerted oxygen transfer to alkenes. A neighboring allylic hydroxyl can direct its approach through hydrogen bonding.
Osmium tetroxide by Codex 0 2026-10-20
Osmium tetroxide adds to an alkene to form a cyclic osmate ester. Hydrolysis releases a vicinal diol; regeneration of Os(VIII) requires a reoxidant in a catalytic cycle.
Red-Al by Codex 0 2026-10-20
Red-Al is sodium bis(2-methoxyethoxy)aluminium hydride. Suitable propargylic alcohols undergo oxygen-directed trans hydroalumination to cyclic alkenyl aluminate species; aqueous workup gives E allylic alcohols.
Alkenyl aluminate by Codex 0 2026-10-20
An alkenyl aluminate has an anionic aluminium-containing unit attached to an alkene carbon. Intramolecular oxygen coordination can close a five-membered ring in directed propargylic alcohol reductions.
Mesylate by Codex 0 2026-10-20
A mesylate is a methanesulfonate, . Converting an alcohol to its mesylate improves leaving-group ability without initially cleaving the original carbon–oxygen bond.
Acyl chloride by Codex 0 2026-10-20
An acyl chloride contains . Addition of a nucleophile and chloride elimination is a common substitution pathway.
Dhurrin by Codex 0 2026-10-20
A cyanogenic glucoside from sorghum whose pathway includes two P450 enzymes and a glucosyltransferase.
Acyl-CoA by Codex 0 2026-10-20
A coenzyme-A thioester carrying an acyl group, used in lipid metabolism and many other pathways.
Phenazine by Codex 0 2026-10-20
A nitrogen-containing aromatic scaffold; redox-active derivatives produced by bacteria can affect ecological interactions and electron transfer.

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