Kosher alkene to ketone method?

interrupt · Thu Mar 03, 2005 5:47 pm

Just read a collection of posts (don't know how old...) dealing with acid-catalysed hydration of alkenes. Like it lots, especially the parts written by a chemist called tBOC. Anyone know if this is a valid pathway from alkene to MDP2Pol to MDP2P?

Ta.

Guest · Thu Mar 03, 2005 6:05 pm

A few years back, when that was written, 7 , to be rough,
Alot of hype and much attention was infact focused into this proceedure,
In fact, it was one of the earliest of questions, at the hive, when it begun,

In theory Safrole could have to taken to mdp2p via the mdp2pol, using reagents as simple as h2so4 alone,

Tboc had some very contrversial posts, his theory did seem good, but it just couldn't be repeated in a lab,
Many variations sprang from this, with some success,
There was a magic oxider, from memory that completed the mdp2pol to mdp2p,,
Like ghosts they still roam the archives,
Whether or not it actually has worked is beyound my knolwedge,
But apparently it is possible,

It will be interesting to see, any futher results

syn

interrupt · Thu Mar 03, 2005 7:17 pm

Thanks synthetika.

It's certainly a fascinating route - the old posts really leap-out at one in terms of elegance and simplicity. I may have to investigate.

On tBOC, his posts (the ones I have read on this alkene hydration) are stylishly written and for me, have more than a ring of truth about them. He certainly doesn't come over as a fraud but I hear what you say about his chemistry being unrepeatable.

Anyone else have anything to report on this, especially on the tBOC posts?

Cheers

CherrieBaby · chouchou

I wouldn't bother with that MDP2Pol route if I were you.

If you're looking for something novel (and easier) you could try epoxidation using percarbonate or perborate rather than peroxy acid. The perborate route will be a better workup because there is no need to distill off corrosive acids (performic) using a vacuum pump (potentially damaging your pump). But, most likely, a percarbonate epoxidation will have to be done under PTC. No problem, you can extract PTCs from several household products.

There are some references to PDFs describing these reagents from Rhodium's site here: Review: Epoxidations of Alkenes with H2O2

These PDFs may still be available on one of the ScienceMadness FTPs. I shall hunt them down.

interrupt · Mon Mar 07, 2005 4:55 pm

I would be very interested in information on the epoxidation route but how OTC is it? My initial interest in the MDP2Pol research by tBOC et al was its OTCness.

This morning I came across another route: peracid oxidation.

http://12.162.180.114/dcd/chemistry/peracid.html

then there is another document suggesting a better rearrangement of the glycol stage using HCl rather than H2SO4.

https://www.synthetikal.com/synthforum/viewtopic.php?t=274

BAsically, the mission is for the best, OTC route from sassafras oil to MDP2P

Thanks

IndoleAmine · Dreamreader Deluxe

If you're looking for this: yes, you found the most otc route to MDP2P, all by yourself. congrats!
(then again, its not that hard to find..)

safrole -KOH-> isosafrole -H2O2/HCOOH-> glycol/epoxide -HCl-> MDP2P..
Wink

i_a

interrupt · Tue Mar 08, 2005 1:47 pm

If only I had found organic chemistry this absorbing while still at school... Wink