Hydrolysis of medium-ring phosphates. Mechanism of rate acceleration by an amino group
RK Sharma, R Vaidyanathaswamy
Index: Sharma, Ravinder K.; Vaidyanathaswamy, Ramamoorthy Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1741 - 1745
Full Text: HTML
Citation Number: 4
Abstract
A series of 2-oxo-2-(p-nitrophenoxy)-1, 3-dioxa-2-phosphacyclmtane derivatives (1-5) having either a nitrogen or a sulfur atom placed transannularly in the ring were synthesized, and their rates of hydrolysis were examined. The pH-rate profile shows that while 1 undergoes hydrolysis over a wide pH range, others are hydrolyzed at a significant rate only in basic medium, thus implicating the amino function for rate enhancement. By ...
Related Articles:
2, 4-Dinitrophenol as an activating reagent in a facile preparation of cyclic phosphate triesters
[Amigues, Eric J.; Migaud, Marie E. Tetrahedron Letters, 2004 , vol. 45, # 5 p. 1001 - 1004]
A convenient synthesis of 6-, 7-, and 8-membered cyclic phosphodiesters
[Ramirez, Fausto; Tsuboi, Hikotada; Okazaki, Hiroshi; Marecek, James F. Tetrahedron Letters, 1982 , vol. 23, # 51 p. 5375 - 5376]
[Jankowska, Jadwiga; Stawinski, Jacek Synthesis, 1984 , # 5 p. 408 - 410]
2, 4-Dinitrophenol as an activating reagent in a facile preparation of cyclic phosphate triesters
[Amigues, Eric J.; Migaud, Marie E. Tetrahedron Letters, 2004 , vol. 45, # 5 p. 1001 - 1004]