Author Topic: allylbenzene byzantine  (Read 574 times)

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obituary

  • Guest
allylbenzene byzantine
« on: August 08, 2001, 05:58:00 AM »
This proposed synth is not supposed to be a well... efficient or in good yeilds, just a proposal to see if it is possible

Styrene + Br2/CCl4 --> 1,2-dibromophenylethane (A)
A + 2NaNH2/NH3 --> phenylacetylene (B)
B + NaH or NaNH2 --> sodium phenylacetylide (C)
C + MeI --> allylbenzene 

definitely long winded for the product, but just a fun idea.

Rhodium

  • Guest
Re: allylbenzene byzantine
« Reply #1 on: August 08, 2001, 12:36:00 PM »
Why would the initially formed Ph-CC-CH3 rearrange to Ph-CH2-CH=CH2? Am I overlooking something?

obituary

  • Guest
Re: allylbenzene byzantine
« Reply #2 on: August 08, 2001, 08:33:00 PM »
ooops, meant propenyl benzene, not allylbenzene.
sorry the idea came very late last night.

Rhodium

  • Guest
Re: allylbenzene byzantine
« Reply #3 on: August 08, 2001, 09:08:00 PM »
I still think you will end up with propynylbenzene, not propenylbenzene. Propynylbenzene is Ph-CC-CH3 with a triple bond in the middle, not a double bond as in propenylbenzene.

obituary

  • Guest
Re: allylbenzene byzantine
« Reply #4 on: August 08, 2001, 10:34:00 PM »
you're correct again, sorry about the confusion- still with a hydrogenation procedure, you could get the allylbenzene- keep in mind obit isn't after yeild here.

obituary

  • Guest
Re: allylbenzene byzantine
« Reply #5 on: August 08, 2001, 10:42:00 PM »
is it possible to take the
propynylbenzene + 2HX --> gem dihalide, 
then gem. dihalide + OH- --> gem. diol
which will automatically lose water to give the ketone, P2P.  (and Phenyl ethyl ketone) ???