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Deprotection by Acidolysis Benzyl-Based Protectors

FIGURE 3.5 Deprotection of functional groups by acidolysis.5 Protonation followed by car-bocation formation during the removal of benzyl-based protectors by hydrogen bromide. Two mechanisms are involved in generating benzyl bromide from the protonated substrates. [Pg.70]

D Ben-Ishai, A Berger. Cleavage of N-carbobenzoxy groups by dry hydrogen bromide and hydrogen chloride. J Org Chern 17, 1564, 1952. [Pg.70]

D Ben-Ishai. The use of hydrogen bromide in acetic acid for the removal of car-bobenzoxy groups and benzyl esters of peptides. J Org Chem 19, 62, 1954. [Pg.70]

Y Kiso, K Ukawa, T Akita. Efficient removal of /V-bcnzyloxycarbonyl group by a push-pull mechanism using thioanisole-trifluoroacetic acid, exemplified by a synthesis of Met-enkephalin. Chem Commun 101, 1980. [Pg.71]


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