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Topic: -CH2Cl to -CHO reaction name  (Read 8217 times)

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Offline Rakkoonn

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-CH2Cl to -CHO reaction name
« on: December 04, 2009, 12:26:15 PM »
Hi,

What's the name of a rection (it's the name of its founder) that leads from -CH2Cl to -CHO group with DMSO and NaHCO3. For example in Chloromethylstyrene

thanks in advance

Offline stewie griffin

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Re: -CH2Cl to -CHO reaction name
« Reply #1 on: December 04, 2009, 02:59:18 PM »
That would be the Cornforth oxidation

Offline stewie griffin

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Re: -CH2Cl to -CHO reaction name
« Reply #2 on: December 04, 2009, 03:10:17 PM »
Hmmm, when I type Cornforth into google, I don't get oxidation of alkyl halides with DMSO. However, I checked my graduate level notes for the Cornforth oxdiation, and directly from the prof's notes, it says the Cornforth reaction is the oxidation of alkyl halides with pyridinium oxide/triethylamine. Right below that is a Cornforth variation where an epoxide is converted to a alpha hydroxy ketone with DMSO. So...I always thought that alkyl halide to carbonyl was a Cornforth oxidation.

Offline Rakkoonn

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Re: -CH2Cl to -CHO reaction name
« Reply #3 on: December 04, 2009, 06:09:25 PM »
Thanks for the help so far, I'm pretty sure the name begins with an "f", like fraschet or so, can't google it thou.

Offline orgopete

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Re: -CH2Cl to -CHO reaction name
« Reply #4 on: December 04, 2009, 11:51:07 PM »
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline stewie griffin

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Re: -CH2Cl to -CHO reaction name
« Reply #5 on: December 05, 2009, 09:26:02 AM »
Ah thanks orgopete! I'll have to change that in my notes. I guess "Kornblum" is close enough to "Cornforth" for a prof to type their notes up incorrectly???  ;)

Offline orgopete

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Re: -CH2Cl to -CHO reaction name
« Reply #6 on: December 05, 2009, 01:39:49 PM »
No, Cornforth is also correct, sort of. There are several ways of dehydrating DMSO and I don't recall whose is which or the order of their discovery. Basically, you are looking at a DMSO oxidation. The Kornblum uses a different method of generating the same intermediate.
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Offline Rakkoonn

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Re: -CH2Cl to -CHO reaction name
« Reply #7 on: December 07, 2009, 12:54:00 AM »
Ok, thanks for all the help

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