The Journal of Organic Chemistry
Note
(
12) The protonated form of intermediate 5 was identified by LCMS
ACKNOWLEDGMENTS
We thank David Kronenthal, Robert Waltermire, Francisco
■
analysis from reaction mixtures. Its structure was corroborated by
comparison with the independently synthesized material.
(
Gonzal
́
ez-Bobes, Lopa Desai, Peng Geng, Jing Liang, and Annie
13) Analysis of the initial rates between −20 and 20 °C provides an
Tam for helpful discussions during the preparation of the
manuscript. We also acknowledge the analytical support
provided by Jingpin Jia, Jonathan Marshall, Curtis Tinker,
and Alice Yang during the development of this work.
activation energy E = 16 ± 1 kcal/mol in line with related hydrolyses
a
of aromatic methyl esters: Mitton, C. J.; Schowen, R. L.; Gresser, M.;
Shapley, J. J. Am. Chem. Soc. 1969, 91, 2036−2044.
(14) Rate data and parameters for the Hammett plot are archived in
Supporting Information. For a discussion of related Hammett plots on
ester aminolyses, see: Knowlton, R. C.; Byers, L. D. J. Org. Chem.
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4
(
(
8
(
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̈
4c,f
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(
(
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(
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