Journal of Organic Chemistry p. 3853 - 3858 (1989)
Update date:2022-08-17
Topics:
Kemp, D. S.
Buckler, David R.
Galakatos, Nicholas George
Kerkman, Daniel
A first study is reported of optimization of a template bridging an oxygen ester with mercury that facilitates intramolecular O,N-acyl transfer from a phenolic oxygen to the amino group of a cysteine residue that is functionalized at sulfur as an arylmercuri complex.Respective effective molarities (EM values) of 0.28, ca. 0.6, and 0.0 are observed for the following three arylmercuri complexes: methyl S-((4-acetoxy-6-phenoxathiinyl)mercuri)-L-cysteinate (9), methyl S-((5-acetoxy-1,3-dimethoxy-2-methyl-9-oxoxanth-4-yl)mercuri)-L-cysteinate (10), and methyl S-((4-acetoxydibenzofuran-6-yl)mercuri)-L-cysteinate (11).Syntheses of these compounds are reported, and the structural significance of the EM values for transition states of the acyl-transfer reactions is discussed.The observed reactivity pattern is consistent with a linear geometry at the mercury atom and a geometry about the forming C-N bond of other than the trans, anti relationship that has been observed for intermolecular acyl-transfer reactions.
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