Journal of Organic Chemistry p. 1741 - 1745 (1982)
Update date:2022-08-05
Topics:
Sharma, Ravinder K.
Vaidyanathaswamy, Ramamoorthy
A series of 2-oxo-2-(p-nitrophenoxy)-1,3-dioxa-2-phosphacyclooctane 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 comparison with rates obtained with 2 and 3 and the quarternary derivative 4, a mechanism involving rate-determining proton transfer from nitrogen to phosphoryl oxygen has been proposed for the hydrolysis of 1 at an acidic pH.The enhancement in the rate of spontaneous hydrolysis of the same compound, however, is explained by a combination of intramolecular general-base and nucleophilic catalysis.
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Doi:10.1039/P19810002906
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