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Topic: pivaloyl chloride  (Read 4437 times)

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Offline MonkeyDust

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pivaloyl chloride
« on: April 16, 2009, 11:32:05 AM »
can pivaloyl chloride (trimethylacetyl chloride) produce a t-butyl cation, in the presence of AlCl3 ??

Offline Squirmy

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Re: pivaloyl chloride
« Reply #1 on: April 16, 2009, 12:35:20 PM »
Yes, this happens to some extent, giving mixtures of acylated and alkylated material.

Can you show a mechanism for formation of the t-butyl cation?

Offline MonkeyDust

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Re: pivaloyl chloride
« Reply #2 on: April 16, 2009, 12:53:43 PM »
well i thought that AlCl3 could coordinate to the oxygen and any free Cl- could attack the carbonyl to give a tetrahedral centre and then the bond between the carbonyl carbon and the alpha carbon could undergo heterolytic fission to give a t-butyl cation and a stabilised carbanion, but this sounds far-fetched.

Offline Squirmy

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Re: pivaloyl chloride
« Reply #3 on: April 16, 2009, 02:03:24 PM »
A hint: one of the byproducts is a gas.

Offline MonkeyDust

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Re: pivaloyl chloride
« Reply #4 on: April 17, 2009, 08:15:23 AM »
carbon monoxide? AlCl3 removes Cl- to give acylium, lose CO to give cation?

Offline Squirmy

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Re: pivaloyl chloride
« Reply #5 on: April 17, 2009, 09:25:54 AM »
That sounds a lot better.

Offline MonkeyDust

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Re: pivaloyl chloride
« Reply #6 on: April 17, 2009, 11:29:50 AM »
cheers

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