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Topic: cyclopentadiene  (Read 5074 times)

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Offline shrikantvarma

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cyclopentadiene
« on: July 20, 2010, 12:59:34 PM »
How to prepare cyclopentadiene in laboratory from its dimer,what are the properties of it ?
« Last Edit: July 20, 2010, 01:23:22 PM by shrikantvarma »

Offline discodermolide

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Re: cyclopentadiene
« Reply #1 on: July 20, 2010, 01:11:30 PM »
You need to distill it at high temperature and trap the distillate at low temperature, -78°C or lower or trap it with another dieneophile. You could trap it into liqud N2. nThis won't be easy.
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Offline stevet

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Re: cyclopentadiene
« Reply #2 on: July 20, 2010, 02:20:31 PM »
If I'm not mistaken, Organic Syntheses has a really good procedure for this reaction. Just search for it, and it gives you all the detail, including hazards etc. I had it for one of my projects, but not sure where it is now, so can't give the exact reference.

Offline OC pro

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Re: cyclopentadiene
« Reply #3 on: July 20, 2010, 02:41:07 PM »
Here you go with the link:

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0238

The set-up is quite easy. You don´t have to cool the trap to -78°C, ice will also do the job. You should use the fresh distilled cyclopentadiene immediately.

Offline ardbeg

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Re: cyclopentadiene
« Reply #4 on: July 20, 2010, 09:07:06 PM »
it smells delightful.  beware.

Offline jchan123

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Re: cyclopentadiene
« Reply #5 on: July 25, 2010, 05:03:35 AM »
As you know, you'll be essentially performing a retro Diels-Alder reaction so if you let your freshly distilled cyclopentadiene (CP) sit around for too long it will re-dimerize.  Just to let you know I've kept CP at -20 oC for over two weeks and only 10% re-dimerizes. So you do have a bit of time and don't necessarily need to use it immediately.

Jeff

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