morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
1,2-benzoquinone
I want to do some hetero diels-alder reaction with 1,2-benzoquinone acting as diene to produce substituted dioxane ring. Will this reaction work? What
should be used as catalyst and solvent (I was thinking of ZnCl2 in xylene). Second, can be catechol oxidised by NaClO to 1,2-benzoquinone in good
yelds or should be used some weaker oxidising agent.
|
|
|
Boffis
International Hazard
Posts: 1836
Registered: 1-5-2011
Member Is Offline
Mood: No Mood
|
|
I am not sure about the Diels-Alder reaction but preparing un-substituted o-benzoquinone requires anhydrous condition to get a good yield, I am not
sure of the exact conditions but silver oxide is the usual oxidant for laboratory isolation of o-benzoquinone from catechol. However, looking at this
paper various other oxidants are mentioned:
Hypochlorite certainly does not give workable yields of quinone in aqueous conditions.
Attachment: 0285.pdf (42kB)
This file has been downloaded 254 times
[Edited on 1-11-2016 by Boffis]
|
|
|
CuReUS
National Hazard
Posts: 928
Registered: 9-9-2014
Member Is Offline
Mood: No Mood
|
|
Quote: Originally posted by morsagh  | | I want to do some hetero diels-alder reaction with 1,2-benzoquinone acting as diene to produce substituted dioxane ring. Will this reaction work?
|
Firstly,I think you want to make a dioxin,not a dioxane.Secondly,whether the diels alder reaction will work or not depends on your alkene
| Quote: | | as a highly reactive 8π-electron system, o-quinones display two 4π components as potential sites for Diels–Alder reactions.The selectivity between
sites results from the polarizability of the complementary 2π component. For example, polarized alkenes such as enamines add to the external dione to
restore aromaticity and yield a dioxin,while less polarized alkenes such as styrene add to the cyclohexadiene portion to yield a [2.2.2]bicyclooctane
|
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1557836/
| Quote: | | 1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution |
https://en.wikipedia.org/wiki/1,2-Benzoquinone
wiki gives the above paper as a reference for the oxidation but I couldn't find it mentioned anywhere in that paper.
|
|
|
morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
I´ve got good dienophille, i am more worried about oxidation of catechol to o-benzoquinone, why shouldn´t NaClO catalysed by Fe3+ work?
|
|
|
Nicodem
|
Thread Moved
3-11-2016 at 08:58 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
