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Topic: How to Cleave O-Ph Bond ?  (Read 3064 times)

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Offline loginprakash

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How to Cleave O-Ph Bond ?
« on: June 08, 2012, 05:18:35 AM »
What is the best method to break a O-Ph bond, specially when it is in the anomeric position of a sugar ? That too with a non participating neighbouring group(azide)

Offline discodermolide

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Re: How to Cleave O-Ph Bond ?
« Reply #1 on: June 08, 2012, 08:24:24 AM »
What is the best method to break a O-Ph bond, specially when it is in the anomeric position of a sugar ? That too with a non participating neighbouring group(azide)

A O-Ph bond will be hard to break. You might post the structure if you can?
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Offline loginprakash

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Re: How to Cleave O-Ph Bond ?
« Reply #2 on: June 08, 2012, 08:38:56 AM »
i can send the structure ..but presently there r some problems to attach the image..in the server i suppose...will send it after it is resolved..

Offline loginprakash

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Re: How to Cleave R-OPh Bond ?
« Reply #3 on: June 08, 2012, 09:49:39 AM »
I am sorry it is not the O-Ph bond it is the R-OPh bond !!!

Offline Guitarmaniac86

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Re: How to Cleave O-Ph Bond ?
« Reply #4 on: June 08, 2012, 09:54:44 AM »
Is the group O-Ph or O-CH2-Ph, because the latter can be cleaved by hydrogenation as it is an OBn group, O-Ph will be harder to cleave.

Is the reaction a glycoside that you are deprotecting?
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Offline nox

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Re: How to Cleave O-Ph Bond ?
« Reply #5 on: June 09, 2012, 01:46:27 AM »
This Science paper from the Hartwig group might be of interest to you:

Selective, Nickel-Catalyzed Hydrogenolysis of Aryl Ethers

http://www.sciencemag.org/content/332/6028/439.abstract

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