Nucleophilic substitutions at the pyridine ring. Conformational preference of the products and kinetics of the reactions of 2-chloro-3-nitro-and 2-chloro-5-nitro-pyridines …

EA Hamed, AA El-Bardan, EF Saad…

Index: Hamed, Ezzat A.; El-Bardan, Ali A.; Saad, Esmat F.; Gohar, Gamal A.; Hassan, Ghada M. Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 11 p. 2415 - 2421

Full Text: HTML

Citation Number: 29

Abstract

The reactions of 2-chloro-3-nitropyridine 1 and 2-chloro-5-nitropyridine 2 with arenethiolates 3a–i result in arylthio-dechlorination to give 2-arylthio-3-nitropyridines 4a–i and 2-arylthio-5- nitropyridines 5a–i. A 1H NMR study and AM1 calculations of 5a–i have shown that these compounds assume a skew conformation except the 2-(4-nitrophenylthio) derivative 5f which has a twist one. An addition–elimination mechanism is suggested based on second ...