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Topic: Decatrien heating  (Read 4211 times)

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Offline nanotube

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Decatrien heating
« on: January 12, 2012, 05:45:19 AM »
Hi,

I recently saw a following, small question, where I really wasn't sure about:
What would happen to 3-methyl 1,3,9 decatriene is we would heat it up (nothing else present in the solution) ?
1,3,9 decatriene  :rarrow: :delta: :rarrow: ?

I was thinking it would spontaneously form two bound 6-cyclic & 5-cylcic structure.

Thx in advance

Offline Dan

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Re: Decatrien heating
« Reply #1 on: January 12, 2012, 06:18:47 AM »
I was thinking it would spontaneously form two bound 6-cyclic & 5-cylcic structure.

You are on the right track, are you suggesting bicyclo[4.3.0]non-2-ene? I think you have lost a carbon atom in your molecule, have another shot...
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Offline nanotube

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Re: Decatrien heating
« Reply #2 on: January 12, 2012, 07:14:41 AM »
You are on the right track, are you suggesting bicyclo[4.3.0]non-2-ene? I think you have lost a carbon atom in your molecule, have another shot...

No no, more something like this :

Offline Dan

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Re: Decatrien heating
« Reply #3 on: January 12, 2012, 07:18:32 AM »
Can you draw a sensible mechanism for that reaction? You are not on the right track.

How to dienes normally react with alkenes when heated?
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Offline discodermolide

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Re: Decatrien heating
« Reply #4 on: January 12, 2012, 10:15:18 AM »
You are on the right track, are you suggesting bicyclo[4.3.0]non-2-ene? I think you have lost a carbon atom in your molecule, have another shot...

No no, more something like this :


Think about Diels-Alder reactions
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