Acetylation of nucleosides by N-acetoxy-N-arylacetamides: dependence on base, aryl group, and buffer composition

…, DL Smith, E Jenkins, JA McCloskey

Index: Scribner, John D.; Scribner, Norma K.; Smith, David L.; Jenkins, Ellen; McCloskey, James A. Journal of Organic Chemistry, 1982 , vol. 47, # 16 p. 3143 - 3145

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Citation Number: 11

Abstract

Figure 4. of solvolysis was due to nitrenium ion generation. The acetylating capability of 6 appears to be due to steric acceleration, since the CO-N-0 plane is forced to be essentially perpendicular to the plane of the naphthalene ring (CPK space-filling models). Direct acetylation by 6 at a significant rate seems simply to require a stronger nucleophile than hydroxyl, thus involving the exocyclic amino group of cytidine. The fact that we did not ...