Kinetics and mechanisms of the reactions of S-methyl chlorothioformate with pyridines and secondary alicyclic amines
EA Castro, M Aliaga, M Gazitúa, JG Santos
Index: Castro, Enrique A.; Aliaga, Margarita; Gazitua, Marcela; Santos, Jose G. Tetrahedron, 2006 , vol. 62, # 20 p. 4863 - 4869
Full Text: HTML
Citation Number: 26
Abstract
The pyridinolysis of S-methyl chlorothioformate shows a biphasic Brønsted-type plot, in agreement with a stepwise mechanism and a change in the rate-limiting step, from formation of a zwitterionic tetrahedral intermediate (T±) at high pKa to its breakdown at low pKa. The reaction of the same substrate with secondary alicyclic amines shows a linear Brønsted-type plot of slope 0.23, which is in accordance with a stepwise mechanism where formation of ...
Related Articles:
[Mizuno, Takumi; Nishiguchi, Ikuzo; Sonoda, Noboru Tetrahedron, 1994 , vol. 50, # 19 p. 5669 - 5680]
[Leung, Man-Kit; Lai, Jun-Liang; Lau, King-Hang; Yu, Hsiao-Hua; Hsiao, Hsiang-Ju Journal of Organic Chemistry, 1996 , vol. 61, # 12 p. 4175 - 4179]
[Mizuno, Takumi; Nishiguchi, Ikuzo; Sonoda, Noboru Tetrahedron, 1994 , vol. 50, # 19 p. 5669 - 5680]
[Castro, Enrique A.; Aliaga, Margarita E.; Cepeda, Marjorie; Santos, Jose G. International Journal of Chemical Kinetics, 2011 , vol. 43, # 7 p. 353 - 358]
[Mizuno, Takumi; Nishiguchi, Ikuzo; Sonoda, Noboru Tetrahedron, 1994 , vol. 50, # 19 p. 5669 - 5680]