Author Topic: Novel? (Read 135 times)

thesim · « **on:** November 10, 2010, 05:27:26 PM »

This is documented on rhodium but after hours of scanning swim cant find any hive posts on it, can anyone give any notes on it?

Quote

Spent quite a while looking at this and I dont see why it wouldnt work?

Any comments or opinions welcome!

P2P from 3-phenyl-1-chloropropane

Simple dehydrohalogenation to Allylbenzene

And of course Allylbenzene is an oxidation away from our second favourite chemical P2P.

Would love to hear if this is feasable, sounds perfect and OTC if you shop around.

letters · « **Reply #1 on:** November 14, 2010, 05:23:16 PM »

novel or not, you should brush up on your mechanism.
The elimination reaction you are suggesting can happen, but i just cant see it yielding too well. the allylbenzene is not such a gain in enthalpy over the alkylchloride and i suspect yields will be on the low side, if any. Also, while a primary alkyl halide "classically" only undergoes E2 mechanism, I can defiently see how in real-world chemistry, some E1 type transformation might occur with carbocation rearrangement to yield the propenylbenzene.

zzhuchila_clocker · « **Reply #2 on:** November 15, 2010, 07:16:30 AM »

surely, if you use heat and base(or just a base like KOt-Bu), after elimination you'll have same thing as happens to safrole, eugenol and other allylbenzenes with base - rearrangement to propenylbenzene
if you want to avoid it, probably, you may use a Cope elimination of N-oxide of corresponding dimethylamine (ammonia halogen substitution, followed by Eschweiler Clark methylation with CH2O/HCOOH and then H2O2). Or you need to use such kind E2 elimination that avoids using strong bases

Author Topic: Novel? (Read 135 times)

thesim

Novel?

letters

Re: Novel?

zzhuchila_clocker

Re: Novel?