Inorganic chemistry,alkynols (hydroxyalkynes) areorganic compounds that contain bothalkyne andalcoholfunctional groups. Thus, as structural features, they have a C≡Ctriple bond and ahydroxyl group. Some alkynols play a role as intermediates in the chemical industry.
The shortened termynol typically refers to alkynols with the hydroxyl group affixed to one of the twocarbon atoms composing the triple bond (C≡C−OH), the triple-bond analogues toenols.[1] Ynols cantautomerize toketenes.
Thedeprotonatedanions of ynols are known asynolates, the triple-bond analogues toenolates.
Alkynols may be formed by thealkynylation of carbonyl compounds, usually in liquid ammonia.[2]
Ynolates are chemical compounds with a negatively charged oxygen atom attached to analkyne functionality.[3] They were first synthesized in 1975 by Schöllkopf and Hoppe via then-butyllithium fragmentation of 3,4-diphenylisoxazole.[4]
Synthetically, they behave asketene precursors orsynthons.
Ynols can interconvert withketenes, much likeenols can withaldehydes andketones. The ynoltautomer is usually unstable, does not survive long, and changes into the ketene. This is becauseoxygen is moreelectronegative thancarbon and thus formsstrongerbonds. For instance,ethynol quickly interconverts withethenone:
| Ynol-ketene tautomers | |
|---|---|
|  |
| Ethynol | Ethenone |
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