Thermal Decomposition of a β -Ketophosphonic Acid

Journal of Organic Chemistry

Volumn 38, Issue 15, 1973, Pages 2721-2722

  Kluger, Ronald ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33747290570     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00955a034     Document Type: Article

References (15)

1. L. F. Fieser and M. Fieser, “Advanced Organic Chemistry,” Reinhold, New York, N. Y., 1961, pp 446-448.
2. W. P. Jencks, “Catalysis in Chemistry and Enzymology,” McGraw-Hill, New York, N. Y., 1969, pp 116-120.
3. K. J. Pedersen, J. Amer. Chem. Soc, 51, 2098 (1929), and references cited therein.
4. F. H. Westheimer and W. A. Jones, J. Amer. Chem. Soc, 63, 3283 (1941).
5. E. J. Corey and T. Durst, J. Amer. Chem. Soc, 88, 5656 (1966).
6. W. W. Butcher and F. H. Westheimer, [J. Amer. Chem. Soc, 77, 2420 (1955)]
7. invoked this species to explain the peculiar pH dependence of the rate of hydrolysis of methyl phosphate, noting that Todd proposed in a lecture in 1954 that metaphosphate was an intermediate in phosphorylation reactions. The current status and applications of the metaphosphate hypothesis have recently been summarized by D. G. Gorenstein [J. Amer. Chem. Soc., 94, 2523 (1972)].
8. R. Kluger and P. Wasserstein, J. Amer. Chem. Soc., 95, 1071 (1973).
9. F. A. Cotton and R. A. Sohunn, J. Amer. Chem. Soc., 85, 2394 (1963).
10. H. I. Jacobson, M. J. Griffith, S. Preis, and E. V. Jensen, J. Amer. Chem. Soc., 79, 2608 (1957).
11. D. E. C. Corbridge and E. J. Lowe, J. Chem. Soc, 493 (1954).
12. E. Thilo, Angew. Chem., Int. Ed. Engl., 4, 1061 (1965).
13. C. R. Hauser and B. E. Hudson, Jr., Org. React., 1, 266 (1942).
14. Note Added in Proof.—P. A. Grieco and C. S. Pogonowski [J. Amer. Chem. Soc, 96, 3071 (1973)] have recently developed methods for alkylation of the 4 position of dimethyl acetonylphosphonate.
15. G. M. Kosolapoff, Org. React., 6, 273 (1951).