I read that cyclohexene/cyclopentene can be converted with N2O to produce cyclohexanon and cyclopentanon and would like to know more about this
procedure. If anyone has experience, please let me know.CharlieA - 22-2-2016 at 06:14
Where is your reference, please?MrMario - 22-2-2016 at 06:31
U need to click on "Look inside" to see the preview of the paper.UC235 - 22-2-2016 at 07:17
The reaction conditions for this are 250C, 100atm in an autoclave.CharlieA - 22-2-2016 at 12:19
Thanks for the link. I don't think that the 250*C is a problem, but 100 atm? How do you propose to develop (and contain) that much pressure? You are a
much braver man than I, Mario. If you try this, please let us know how it turns out-Ciao, CharlieDraconicAcid - 22-2-2016 at 12:43
100 atm of N2O? That's a laugh and a half.
I'm sure it would be much easier to add water across the double bond with dilute sulphuric acid, and then oxidize the alcohol with bleach.
[Edited on 22-2-2016 by DraconicAcid]clearly_not_atara - 22-2-2016 at 21:00
If you just feel like running a vapor-phase reaction, singlet oxygen (which is dangerous) gives 3-hydroperoxycyclopentene. This can be converted into
cyclopentenone in a variety of ways, or directly to more interesting compounds.
Otherwise I believe the traditional answer involves mercury acetate and potassium dichromate.
[Edited on 23-2-2016 by clearly_not_atara]
[Edited on 23-2-2016 by clearly_not_atara]UC235 - 22-2-2016 at 22:20
If you just feel like running a vapor-phase reaction, singlet oxygen (which is dangerous) gives 3-hydroperoxycyclopentene. This can be converted into
cyclopentenone in a variety of ways, or directly to more interesting compounds.
Actually, this can be done in the liquid phase (perhaps diluted in methanol) in oxygen atmosphere using methylene blue or rose bengal as a sensitizer
and a fairly powerful light source. Reduction to the allylic alcohol is trivial involving aq. Na2SO3 or zinc and acetic acidDJF90 - 23-2-2016 at 01:58
Actually, this can be done in the liquid phase (perhaps diluted in methanol) in oxygen atmosphere using methylene blue or rose bengal as a sensitizer
and a fairly powerful light source.
Sooo, i guess it's not something what could be done as a hobby chemist.. Don't think I have the equipment to reach ~100 bar.Dr.Bob - 23-2-2016 at 10:44
Reaching 100 bar is not a problem at all. Containing it in one place is, however. I bet Bert can elaborate on the first step. CuReUS - 24-2-2016 at 03:29
