Ynol

In chemistry, an ynol (or alkynol) is an alkyne with a hydroxyl group affixed to one of the two carbons composing the triple bond.[1] The deprotonated anions of ynols are known as ynolates. An ynol with hydroxyl groups on both sides of its triple bond is known as an ynediol; only one ynediol, acetylenediol, exists.

Ethynol, the simplest ynol

Ynolates
The molecular structure of an ynolate

Ynolates are chemical compounds with a negatively charged oxygen attached to an alkyne functionality.[2] They were first synthesized in 1975 by Schöllkopf and Hoppe via the n-butyllithium fragmentation of 3,4-diphenylisoxazole.[3]

Synthetically, they behave as ketene precursors or synthons.

Ynol–ketene tautomerism

Ynols can interconvert with ketenes, much like enols can with aldehydes and ketones. The ynol tautomer is usually unstable, does not survive long, and changes into the ketene. This is because oxygen is more electronegative than carbon and thus forms stronger bonds. For instance, ethynol quickly interconverts with ethenone:

Ynol-ketene tautomers
EthynolEthenone
gollark: Eh. It's improved. Still problematic though, but I like it.
gollark: Well, it's poorly designed, more so than JS in my opinion.
gollark: PHP is maaaaybe easy for simple stuff, but also very evil.
gollark: There are many languages you can use for web*server*y stuff, but you can only really use HTML/CSS/JS for frontends.
gollark: With Express.js the server thing would look *very roughly* like this:```javascriptconst express = require("express")const multer = require("multer")const app = express()const upload = multer({ storage: multer.memoryStorage(), limits: { fileSize: 2**22 // 4MiB maximum filesize }})app.get("/image", (req, res) => { res.send(loadImageFromSomewhere())})// send upload form HTML - you would need to write this tooapp.get("/upload", (req, res) => res.sendFile("upload.html"))app.post("/upload", upload.single("file"), (req, res) => { saveImageSomewhere(req.file.buffer)})app.listen(8700, () => console.log("listening")) // listen on port 8700```

See also

References
  1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "ynols". doi:10.1351/goldbook.Y06730
  2. M. Shindo (2007). "Synthetic uses of ynolates". Tetrahedron. 63 (1): 10–36. doi:10.1016/j.tet.2006.09.013.
  3. U. Schöllkopf and I. Hoppe (1975). "Lithium Phenylethynolate and Its Reaction with Carbonyl Compounds to Give β-Lactones". Angewandte Chemie International Edition in English. 14 (11): 765. doi:10.1002/anie.197507651.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.