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N-Boc deprotection via phenol 1N et TMSCl 0.33N
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Topic: N-Boc deprotection via phenol 1N et TMSCl 0.33N (Read 7270 times)
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faust
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N-Boc deprotection via phenol 1N et TMSCl 0.33N
«
on:
April 07, 2006, 01:26:47 PM »
Hello,
Just a simple question, do you know what is the mechanism for the N-boc deprotection using phenol and tmscl?
Thank you very much
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Re: N-Boc deprotection via phenol 1N et TMSCl 0.33N
«
Reply #1 on:
April 12, 2006, 02:33:55 PM »
The carbonyl oxygen attacks TMS, then the t-butyl carbocation falls off and gets trapped by the phenol to make t-butyl phenyl ether. The TMS carbamate decomposes in in water to make CO
2
and TMS-OH.
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N-Boc deprotection via phenol 1N et TMSCl 0.33N