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Kinetics and mechanism of decomposition of N ‐chloroamino acids. II: Conformationally restricted models

10.1002/jps.2600791216.abs The kinetics of decomposition of the following conformationally restricted N‐chloro‐α‐amino acids were studied: 1‐amino‐1‐cyclopentanecarboxylic acid (2), 1‐amino‐1‐cyclohexanecarboxylic acid (4), 2‐amino‐2‐norbornanecarboxylic acid (6), and 2‐amino‐2‐benzonorbornanecarboxylic acid (8). The first‐order rate constants obtained were 0.520, 5.197, 0.198, and 0.078, repectively, which correlated with the ring strian in the structurally related cyclic ketones cyclopentanone, cyclohexanone, norborane‐2‐one, and benzonorbornane‐2‐one. The data are supportive of a concerted mechanism for the decomposition reaction involving an imine‐like transition state. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Pharmaceutical Science Wiley

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