Advanced Organic Chemistry by Warren

By Warren

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10 reveals that in these compounds, the ester oxygen is attached to a nitrogen atom that is linked to a double-bonded atom that is either the carbon atom of a carbonyl or the nitrogen atom of a triaza sequence of atoms. Each carbonyl or triaza group bears a pair of unshared electrons. It is the presence of these electrons in the ester moiety in proximity to the carbonyl that is responsible for the high activation. 10). This neighboringgroup participation in the formation of a new chemical bond is referred to as anchimeric assistance.

R Rebek, D Feitler. Mechanism of the carbodiimide reaction. II. Peptide synthesis on the solid support. J Am Chem Soc 96, 1606, 1974. 4. DH Rich, J Singh. The carbodiimide method, in E Gross, J Meienhofer, eds. The Peptides: Analysis, Synthesis, Biology, Academic, New York, 1979, Vol 1, pp 241-261. 5. NL Benoiton. Quantitation and the sequence dependence of racemization in peptide synthesis, in E Gross, J Meienhofer, eds. The Peptides: Analysis, Synthesis, Biology, Academic, New York, 1981, Vol 5, pp 341-361.

Can J Chem 59, 384, 1981. 8. NL Benoiton, FMF Chen. Reaction of N-t-butoxycarbonylamino acid anhydrides with tertiary amines and carbodiimides. New precursors for 2-t-butoxyoxazol-5(4H)-one and N-acylureas. J Chem Soc Chem Commun 1225, 1981. 15). One-half of an equivalent of carbodiimide is employed. 5, path C) can be rationalized in the same way as the reaction of acid with carbodiimide is rationalized; namely, protonation at the basic nitrogen (C=NR3) of the O-acylisourea by the acid, followed by attack at the activated carbonyl of the acyl group by the carboxylate anion.

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