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Topic: Detritylation  (Read 2019 times)

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Offline vamsikrishna

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Detritylation
« on: February 23, 2017, 08:23:18 PM »
W. P. Jencks, J. Am. Chem. Soc., 1972, 94, 4731

Can someone please kindly provide me the above mentioned article. Can someone kindly provide the mechanism for detritylation using catalyst sodium bisulphite.

Offline AWK

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Re: Detritylation
« Reply #1 on: February 23, 2017, 11:59:08 PM »
Trityl is removed in acidic conditions. pH of NaHSO3 is about 4.5. May be this is a simple acid catalysis (if works).
AWK

Offline sjb

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Re: Detritylation
« Reply #2 on: February 24, 2017, 03:04:53 AM »
Looking at the front page, http://pubs.acs.org/doi/pdf/10.1021/ja00768a052 I would concur with AWK

Offline AWK

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Re: Detritylation
« Reply #3 on: February 24, 2017, 03:57:59 AM »
Trityl is used for protection of -OH and -NH2 groups but this information is missing in post of
vamsikrishna.
In link given to one of Jenks 2 pages publication (from series) general consideration on acid-base catalysis are given. From the first page of Jenks reference vamsikrishna can can discuss his/her case, we only can guess.
Deprotection of group consists of two steps: catalysis and reaction. The reaction can be modified or facilitated by solvent and reagent used for deprotection.
AWK

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