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Topic: N-Boc deprotection via phenol 1N et TMSCl 0.33N  (Read 6949 times)

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Offline 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 CO2 and TMS-OH.

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