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Author Topic: Sensitivity of methylenedioxy group  (Read 4258 times)

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Dr_Heckyll

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Sensitivity of methylenedioxy group
« on: August 03, 2002, 08:25:00 PM »
How sensitive is the methylenedioxy group in a simple molecule like methylenedioxybenzene to acid-catalyzed splitting? Will it be split by methanesulfonic acid or acetic acid in a water-free system and prolonged reflux?


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hest

  • Guest
naaa don't think so. HI(aq) will do BF3 will also ...
« Reply #1 on: August 04, 2002, 10:06:00 AM »
naaa don't think so.
HI(aq) will do BF3 will also (or most other lewis acids)
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Flip

  • Guest
Re: Sensitivity of methylenedioxy group
« Reply #2 on: August 04, 2002, 07:10:00 PM »
On a similar note, relating to my current project;

What would be the effects of ozonolysis on a methylenedioxy benzene? Assuming of course the standard controlled conditions are met, the benzene ring is not attacked, and that a dilute O3/O2 mixture is used?  Would the methylenedioxy group even make a difference from the results of an ozonolysis on plain ol' benzene?  This may seem obscure but to me it is quite pertinent.
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Dr_Heckyll

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By instinct rather than by knowledge I would be ...
« Reply #3 on: August 04, 2002, 07:51:00 PM »
By instinct rather than by knowledge I would be worried that the product would be something like












Molecule:

bdo ("O=C2OC1=CC=CC=C1O2")


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PrimoPyro

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Unstable
« Reply #4 on: August 04, 2002, 07:53:00 PM »
This compound is an acid anhydride of carbinic acid and catechol, and would likely hydrolyze in moisture to carbon dioxide and catchol, would it not?
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Flip

  • Guest
please forgive my ignorance
« Reply #5 on: August 04, 2002, 08:10:00 PM »
How exactly would O3 attack the methylenedioxy to form this compound which hydrolyses to CO2 and bezenediol?
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PrimoPyro

  • Guest
It Doesn't
« Reply #6 on: August 04, 2002, 08:19:00 PM »
That compound would not be formed.
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WizardX

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Halogenating Reagents
« Reply #7 on: August 07, 2002, 06:18:00 PM »
Halogenating Reagents: PCl3 or PCl5, PBr3 etc... will halogenate the methylenedioxy ring with halogens.

Reference? Must find it again? Stay tuned!

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Rhodium

  • Guest
methylenedioxy ring chlorination
« Reply #8 on: August 07, 2002, 07:27:00 PM »
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WizardX

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Thanks Rhodium!
« Reply #9 on: August 09, 2002, 07:05:00 PM »
Ahh, yes! That's one. There is also another, in the JOC, I think??
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Antoncho

  • Guest
Ozonolysis
« Reply #10 on: August 25, 2002, 09:06:00 AM »
There was a ref (on the Hive? i think) that described ozonolysis of piperic acid to piperonal - so i think it's not much of a problem, of course having the exact conditions at hand is strongly recommended.



Antoncho
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GC_MS

  • Guest
ozon etc
« Reply #11 on: August 25, 2002, 09:51:00 AM »
As far as SWiM remembers, O3 is active on olefins as isosafrol, where it oxidizes the propenyl pi-bond and converts the propenylbenzene analogue to its benzaldehyde derivative (i.e. isosafrole -> piperonal).
Stability of the methylenedioxybridge: be sure to keep it away from Lewis bases as AlX3 (X=Cl, Br, I) and all those other stuff that can be used for the O-demethylation of methoxybenzene derivatives (such as vanillin, isoeugenol etc). Don't have the exact references and patents handy, but SWiM remembers they are used for the synthesis of 3,4-dimethoxybenzaldehyde and 3,4-dimethoxyphenylpropene from piperonal and (iso)safrole respectively.
Doped(TM) since 19.... euhm... a long time  :)
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