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Interesting rearrangement reaction
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Topic: Interesting rearrangement reaction (Read 3206 times)
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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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azmanam
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Mediocrity is a handrail -Charles Louis d'Secondat
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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azmanam
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Mediocrity is a handrail -Charles Louis d'Secondat
Re: Interesting rearrangement reaction
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Reply #2 on:
February 17, 2009, 04:25:51 PM »
love that rearrangement, though.
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Interesting rearrangement reaction