November 22, 2024, 09:27:38 PM
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Topic: Haloform Reaction  (Read 4123 times)

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Offline vivekrai

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Haloform Reaction
« on: February 21, 2012, 02:56:30 AM »
I'm not able to follow how the Haloform Reaction occurs here.
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Offline vivekrai

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Re: Haloform Reaction
« Reply #1 on: February 21, 2012, 02:59:58 AM »
2. Same problem. Not able to follow up what's happening there
" हर विफल्तापर पर न तुम आँसू बहाओ हर सफलता का यही पहला चरण है | "
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Offline Arctic-Nation

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Re: Haloform Reaction
« Reply #2 on: February 21, 2012, 06:07:50 AM »
1. No idea. Are you sure you're not missing reagents or conditions again?

2. First step is the chlorination of an alpha position. Further reactions might be possible, depending on exact conditions.

Offline AWK

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Re: Haloform Reaction
« Reply #3 on: February 21, 2012, 11:27:38 AM »
Gadi Rothenberg and Yoel Sasson
Extending the Haloform Reaction to non-Methyl Ketones
Tetrahedron, Vol. 52, No. 43, pp. 13641-13648, 1996
AWK

Offline vivekrai

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Re: Haloform Reaction
« Reply #4 on: February 21, 2012, 01:32:26 PM »
Gadi Rothenberg and Yoel Sasson
Extending the Haloform Reaction to non-Methyl Ketones
Tetrahedron, Vol. 52, No. 43, pp. 13641-13648, 1996

I'm looking into it. Edit: But why is it asking me to purchase anything?
" हर विफल्तापर पर न तुम आँसू बहाओ हर सफलता का यही पहला चरण है | "
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Offline discodermolide

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Re: Haloform Reaction
« Reply #5 on: February 21, 2012, 04:01:46 PM »
Gadi Rothenberg and Yoel Sasson
Extending the Haloform Reaction to non-Methyl Ketones
Tetrahedron, Vol. 52, No. 43, pp. 13641-13648, 1996

I'm looking into it. Edit: But why is it asking me to purchase anything?

Because it is Elsivier they charge for copies of every paper that appears in their journals.
Go to your local Uni and see if they have it there.
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Offline orgopete

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Re: Haloform Reaction
« Reply #6 on: February 23, 2012, 10:28:29 AM »
Kudos to AWK!

Again, in line with the commentary here, http://www.chemicalforums.com/index.php?topic=56348.0, I would have expected a simple chlorination of cyclohexanone. Normally this is done in acetic acid, but I thought, okay, water should work. This is where AWK really filled a gap. Is there any difference in a reaction if you leave out one of the reagents?

The abstract gives the product, adipic acid, http://www.sciencedirect.com/science/article/pii/0040402096008162 (note scroll bar to see scheme). This is where AWK really filled the gap. I would never have expected this reaction from the information given, but the prior reaction also was difficult to imagine. It would have been easier if it were the 1,3-dihydroxy arrangement, but putting the two reactions together makes a lot more sense.
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