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Topic: Interesting rearrangement reaction  (Read 2922 times)

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Offline aldoxime_amine

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Interesting rearrangement reaction
« on: February 17, 2009, 04:01:37 PM »
When 1-(hydroxymethyl)-2,5-dimethylcyclopentane is treated with aqueous sulphuric acid, one the major products obtained is 1,2-dimethylcyclohexene. Suggest a mechanistic pathway that might explain the formation of this product.

My mechanism always ends up in 1,4-dimethylcyclohexene.... :(
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Offline azmanam

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Re: Interesting rearrangement reaction
« Reply #1 on: February 17, 2009, 04:25:39 PM »
agreed.  I get 1,4-dimethylcyclohexene.  I don't see a good way to connect skeletal carbon atoms 2 and 5, while simultaneously moving carbon 1 and the exocyclic carbon to between carbon atoms 4 and 5.
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Offline azmanam

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Re: Interesting rearrangement reaction
« Reply #2 on: February 17, 2009, 04:25:51 PM »
love that rearrangement, though.
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