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Topic: Selective Tosylation  (Read 1857 times)

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Offline Aerosolid

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Selective Tosylation
« on: March 25, 2017, 02:57:05 PM »
Hi! I am wondering if anyone knows why the site of triflation changes when this rxn is run in another solvent. (see the attached file for the rxn equation) :).

Offline wildfyr

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Re: Selective Tosylation
« Reply #1 on: March 25, 2017, 03:55:18 PM »
I note that the solvent isn't the only difference. What are your first thoughts? Here we only help those who demonstrate that they have put effort into solving problems themselves.

Offline Aerosolid

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Re: Selective Tosylation
« Reply #2 on: March 25, 2017, 04:35:00 PM »
Yea, well, in the rxn where the pyridone oxygen is tosylated a DTBMP base is applied. I imagine that the base might thoroughly deprotonate the pyridine nitrogen, thus adding a formal negative which would be delocalized onto to the oxygen. But would this make the oxygen more nucleophilic than the nitrogen?

Offline wildfyr

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Re: Selective Tosylation
« Reply #3 on: March 25, 2017, 10:06:54 PM »
I think a phenolate is more nucleophilic than an aniline.

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