08-03-02 20:25
No 340858
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?
Happiness, health and wealth through chemistry...
(Hive Addict)
08-04-02 10:06
No 341206
naaa don't think so.
HI(aq) will do BF3 will also (or most other lewis acids)
(Hive Bee)
08-04-02 19:10
No 341415
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.
(Hive Bee)
08-04-02 19:51
No 341436
By instinct rather than by knowledge I would be worried that the product would be something like
Molecule: bdo ("O=C2OC1=CC=CC=C1O2")
Happiness, health and wealth through chemistry...
(Hive Prodigy)
08-04-02 19:53
No 341438
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?
(Hive Bee)
08-04-02 20:10
No 341444
How exactly would O3 attack the methylenedioxy to form this compound which hydrolyses to CO2 and bezenediol?
(Hive Prodigy)
08-04-02 20:19
No 341447
That compound would not be formed.
(Wizard Master)
08-07-02 18:18
No 342754
Halogenating Reagents: PCl3 or PCl5, PBr3 etc... will halogenate the methylenedioxy ring with halogens.
Reference? Must find it again? Stay tuned!
(Chief Bee)
08-07-02 19:27
No 342790
It's in http://www.orgsyn.org/orgsyn/prep.asp?pr
(Wizard Master)
08-09-02 19:05
No 343750
Ahh, yes! That's one. There is also another, in the JOC, I think??
(Official Hive Translator)
08-25-02 09:06
No 348848
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
(Hive Bee)
08-25-02 09:51
No 348857
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
