Cycloreversions of Anions from Tetrahydrofurans. A Convenient Synthesis of Lithium Enolates of Aldehydes

Journal of Organic Chemistry

Volumn 37, Issue 4, 1972, Pages 560-562

  Bates, R B ^a   Kroposki, L M ^a   Potter, D E ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001043536     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00969a007     Document Type: Article

References (15)

1. Taken in part from the Ph.D. thesis of D. E. P., 1969, and the M.S. thesis of L. M. K., 1970.
2. R. L. Letsinger and D. F. Pollart, J. Amer. Chem. Soc., 78, 6079 (1956), cleaved 2-phenyltetrahydrofuran with propylsodium and after workup obtained (among other products) propane, ethylene, and acetophenone.
3. A. Rembaum, S. P. Siao, and N. Indictor, J. Polym. Sci., 56, 517 (1962), reported that ethyllithium decomposed in THF at 25° to give, among other products, ethylene and the lithium enolate of acetaldehyde.
4. Gilman and coworkers [H. Gilman and G. L. Schwebke, J. Organometal. Chem., 4, 483 (1965), and references cited therein] have measured the rates of decomposition of many organolithium compounds, including n-butyllithium, in THF, but do not report the products in the cases of present interest,
5. S. C. Honeycutt, J. Organometal. Chem., 29, 1 (1971), has recently reported a kinetic study of the cleavage of THF by n-butyllithium.
6. This material, like the starting acid, must be a mixture of dl and meso forms. For earlier preparations of mixtures of these stereoisomers by different methods, see Y.K. Yur'ev and G. Ya. Kondrat'eva, Zh. Obshch. Khim., 24, 1645 (1954), and
7. G. A. Razuvaev and L. S. Boguslavskaya, Zh. Obshch. Khim., 82, 2320 (1962).
8. A. F. Bickel and W. A. Waters, Recl. Trav. Chim. Pays-Bas, 69, 312 (1950).
9. M. F. Ansell, W. J. Hickenbottom, and P. G. Holton, J. Chem. Soc., 349 (1955).
10. B. T. Gillis and P. E. Beck, J. Org. Chem., 28, 1388 (1963).
11. H. Kloosterziel, J. A. A. van Drunen, and P. Galama, Chem. Commun. 885 (1969), report similar values for the potassium salt in NH3 at -60°.
12. S. Oae, W. Tagaki, and A. Ohno, J. Amer. Chem. Soc., 83, 5036 (1961).
13. D. Seebach, Angew. Chem., Int. Ed. Engl., 8, 639 (1969), and references cited therein.
14. J. K. Crandall and L. H. C. Lin, J. Amer. Chem. Soc., 89, 4526 (1967), and references cited therein.
15. R. B. Woodward and R. Hoffmann, Angew. Chem., Int. Ed. Engl. 8, 781 (1969).