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Author Topic: carbonyl compound with a azide connected  (Read 4349 times)

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Doom91

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carbonyl compound with a azide connected
« on: February 18, 2009, 08:17:11 PM »

If there is compound with a azide and carbonyl group in it , what reagents can be used so as to selectively reduce the azide or the carbonyl group Can anyone tell me the conditions and the solvents to carry out such reactions ???
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aldoxime_amine

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Re: carbonyl compound with a azide connected
« Reply #1 on: February 19, 2009, 03:06:05 AM »

Protection of carbonyl and reduction of azide using LAH, hydrolysis will give deprotect the group as well as give product.
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sjb

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Re: carbonyl compound with a azide connected
« Reply #2 on: February 19, 2009, 03:09:00 AM »

What do you want to reduce the azide and carbonyl to? Depending on what you want to do, there are several ways of reducing the carbonyl or the azide.
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Doom91

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Re: carbonyl compound with a azide connected
« Reply #3 on: February 20, 2009, 04:45:15 PM »

reduce the azide to NH2 group and reduce the carbonyl group to OH group
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nj_bartel

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Re: carbonyl compound with a azide connected
« Reply #4 on: February 20, 2009, 09:51:47 PM »

Wait, you want to reduce both?
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kiwi

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Doom91

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Re: carbonyl compound with a azide connected
« Reply #6 on: February 22, 2009, 07:17:58 PM »

either on of them
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sjb

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Re: carbonyl compound with a azide connected
« Reply #7 on: February 23, 2009, 01:45:06 AM »

So basically, you're after chemoselective reduction of either carbonyl, or azide?

Kiwi's idea of the Staudinger is fine as far as I know for the azide, but I can't think of anything that will chemoselectivity reduce the carbonyl to the alcohol - silanes, perhaps?

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nj_bartel

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Re: carbonyl compound with a azide connected
« Reply #8 on: February 23, 2009, 03:09:53 AM »

Does the wolff-kishner affect azides?
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sjb

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Re: carbonyl compound with a azide connected
« Reply #9 on: February 23, 2009, 03:28:17 AM »

I don't think so, but doesn't the W-K take >C=O to >CH2, rather than >CHOH ?

S
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nj_bartel

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Re: carbonyl compound with a azide connected
« Reply #10 on: February 23, 2009, 05:10:31 AM »

Yes it does, sorry - just reread the original post, not down the thread; forgot he wanted an alcohol.
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alexjaco

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Re: carbonyl compound with a azide connected
« Reply #11 on: February 23, 2009, 05:21:49 AM »

You can reduce the azide with hydrogen follwed by LAH to reduce the ketone and you will be left and with alcohol and amine if the above posts wont work with your molecule.
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kiwi

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Re: carbonyl compound with a azide connected
« Reply #12 on: February 24, 2009, 02:52:52 AM »

So basically, you're after chemoselective reduction of either carbonyl, or azide?

Kiwi's idea of the Staudinger is fine as far as I know for the azide, but I can't think of anything that will chemoselectivity reduce the carbonyl to the alcohol - silanes, perhaps?



I personally can't see anything wrong with one of these to selectively reduce the carbonyl:

http://www.organic-chemistry.org/namedreactions/meerwein-ponndorf-verley-reduction.shtm
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kiwi

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Re: carbonyl compound with a azide connected
« Reply #13 on: February 24, 2009, 02:56:41 AM »

You can reduce the azide with hydrogen follwed by LAH to reduce the ketone and you will be left and with alcohol and amine if the above posts wont work with your molecule.

skip the H2 - lithal will reduce both the ketone and the amine
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sjb

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Re: carbonyl compound with a azide connected
« Reply #14 on: February 25, 2009, 11:57:04 PM »

I personally can't see anything wrong with one of these to selectively reduce the carbonyl:

http://www.organic-chemistry.org/namedreactions/meerwein-ponndorf-verley-reduction.shtm

Ahh, nice one!
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