engleski

Acylation of purines and pyrimidines: regioselectivity vs. regiospecificity

Only one product (N1-isomer) was formed in the reaction between pyrimidine anions and FcCOCl in N, N-dimethylformamide. In contrast to the observed regiospecificity in pyrimidine series, the ferrocenoylation of purines is regioselective. In the course of the reaction between purine anions and FcCOCl, the N7- and N9-isomers were detected spectroscopically and isolated thereafter. Steric and electronic effects underlying the mechanistic difference between the purine/pyrimidine nucleobases are explained by use of computational techniques.

nucleobase, ferrocene, NMR, DFT

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