Efficient synthesis and hydrolysis of cyclic oxalate esters of glycols

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 3, 2002, Pages 346-353

  Itaya, Taisuke ^a   Iida, Takehiko ^a   Gomyo, Yasuko ^a   Natsutani, Itaru ^a   Ohba, Masashi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

1,1 oxalyldiimidazole; 1,4 dioxane 2,3 dione hydrolysis; Glycol cyclocondensation; Oxalate hydrolysis kinetics; Oxalyl chloride; Stereoelectronic effect

Indexed keywords

1,1' OXALYLDIIMIDAZOLE; 1,2 CYCLOPENTANEDIOL; 1,4 DIOXANE 2,3 DIONE; 1,4 DIOXANE DERIVATIVE; ACETIC ACID; ACETONITRILE; ALKYL GROUP; BUFFER; CARBONIC ACID; CHLORIDE; COLLIDINE; CYCLOPENTANE DERIVATIVE; DIETHYLOXALIC ACID; ESTER DERIVATIVE; GLYCOL; IMIDAZOLE DERIVATIVE; OXALIC ACID DERIVATIVE; PHENYL GROUP; POLYMER; PYRIDINE; TRIETHYLAMINE; UNCLASSIFIED DRUG; ESTER;

ARTICLE; HYDROLYSIS; KINETICS; PH; PINACOL REARRANGEMENT; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

ESTERS; GLYCOLS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; OXALATES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0036515537     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.346     Document Type: Article

References (32)

1. Jones G. I. L., Owen N. L., J. Mol. Struct., 18, 1-32 (1973).
2. a) Stäglich P., Thimm K., Voß J., Justus Liebigs Ann. Chem., 1974, 671-689;
3. b) Katon J. E., Lin S.-L., J. Mol. Struct., 48, 335-342 (1978);
4. c) Jones G. P., Cornell B. A., Horn E., Tiekink E. R. T., J. Crystallogr. Spectrosc. Res., 19, 715-723 (1989).
5. Schmidt S. P., Schuster G. B., J. Org. Chem., 43, 1823-1824 (1978).
6. a) Wimmer T., Ger. Offen. 2,263,814 [Chem. Abstr., 79, 79182y (1973)];
7. b) Marhold A., Klauke E., Ger. Offen. DE 3,329,126 [Chem. Abstr., 103, 22602v (1985)];
8. c) Nakayama S., Ikeda F., Eur. Pat. Appl. EP 261,977 [Chem. Abstr., 109, 54784w (1988)].
9. a) Verter H. S., Potter H., Dominic R., Chem. Commun., 1968, 973-974;
10. b) Forgione P. S., U. S. 3,431,278 [Chem. Abstr., 70, 96396c (1969)];
11. c) Steglich W., Schmidt H., Hollitzer O., Synthesis, 1978, 622-624.
12. a) Carothers W. H., Arvin J. A., Dorough G. L., J. Am. Chem. Soc., 52, 3292-3300 (1930) and earlier references cited therein;
13. b) Davies A. G., Hua-De P., Hawari J. A.-A., J. Organomet. Chem., 256, 251-260 (1983).
14. Ripley L. G., Watson R. W., Can. J. Chem., 29, 970-973 (1951).
15. White R. C., Tetrahedron Lett., 21, 1021-1022 (1980).
16. Lloyd W. D., Navarette B. J., Shaw M. F., Org. Prep. Proced. Int., 7, 207-210 (1975).
17. a) Hauck F. P., U. S. 3,943,149 [Chem. Abstr., 85, 62847v (1976)];
18. b) Hauck F. P., Idem, U. S. 4,082,773 [Chem. Abstr., 89, 108823x (1978)];
19. c) Roseman S., Link K. P., Carbohydr. Res., 69, 301-304 (1979).
20. Ellingboe E. K., Melby L. R., U. S. 2,816,287 [Chem. Abstr., 52, P12899g (1958)].
21. Jäger V., Schohe R., Paulus E. F., Tetrahedron Lett., 24, 5501-5504 (1983).
22. a) Itaya T., Iida T., Eguchi H., Chem. Pharm. Bull., 41, 408-410 (1993);
23. b) Iida T., Itaya T., Tetrahedron, 49, 10511-10530 (1993).
24. Itaya T., Iida T., Natsutani I., Ohba M., Chem. Pharm. Bull., 50, 83-86 (2002).
25. Itaya T., Iida T., J. Chem. Soc., Perkin Trans. 1, 1994, 1671-1672.
26. This method was also unsuccessful in the preparation of 2l from cis-1,2-cyclopentanediol (1l).
27. When 2,4,6-collidine was employed, the estimated yields of 2o and the oxalate polymers were 29% and 71%, respectively.
28. This structure was supported by X-ray crystallographic analysis: Iida T., Ph. D. Dissertation, Kanazawa University, January 1994.
29. Buist G. J., Bunton C. A., Miles J. H., J. Chem. Soc., 1957, 4567-4574.
30. Hayashi M., Terashima S., Koga K., Tetrahedron, 37, 2797-2803 (1981).
31. For example, see Bunnett J. F., "Investigation of Rates and Mechanisms of Reactions," 3rd ed., Part I, ed. by Lewis E. S., John Wiley and Sons, New York, 1974, pp. 145-153.
32. For neutral hydrolysis of diethyl oxalate (12) in aqueous organic solvents, see Geheb D., Kasanskaja N. F., Beresin I. W., Ber. Bunsenges. Phys. Chem., 76, 160-169 (1972).