Electrocatalyzed addition of dialkyl phosphonates to aromatic carbonyl compounds. A convenient preparation of phosphoric esters via an efficient rearrangement

Electrochimica Acta

Volumn 42, Issue 13-14, 1997, Pages 2225-2231

  Kimura, Makoto ^a   Kurata, Tsunehiko ^a   Yamashita, Tsutomu ^a   Kawai, Hirotaka ^a   Sawaki, Yasuhiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Catalytic reaction; Dialkyl phosphonates; Electroreduction; Rearrangement; Trialkyl phosphates

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; CATALYSIS; CHEMICAL BONDS; ELECTROLYSIS; KETONES; REACTION KINETICS; REDUCTION; SYNTHESIS (CHEMICAL);

DIALKYL PHOSPHONATES; PHOSPHORIC ESTERS; TRIALKYL PHOSPHATES;

PHOSPHORUS COMPOUNDS;

EID: 0030697727     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0013-4686(97)85503-X     Document Type: Article

References (38)

1. Methoden der Org. Chem. (Edited by Houben-Weyl) Bd. XII/1, p. 475, Tieme, Stuttgart (1963).
2. A. N. Pudovik and M. G. Zimin, Pure Appl. Chem. 52, 989 (1980).
3. F. Texier-Boullet and A. Foucaud, Synthesis 165 (1982); F. Texier-Boullet and M. Lequitte, Tetrahedron Lett. 27, 3515 (1986) and references cited therein.
4. F. Texier-Boullet and A. Foucaud, Synthesis 165 (1982); F. Texier-Boullet and M. Lequitte, Tetrahedron Lett. 27, 3515 (1986) and references cited therein.
5. T. Arai, M. Bougauchi, H. Sasaki and M. Shibasaki, J. Org. Chem. 61, 2296 (1996).
6. H. Timmer and J. Kurz, Chem. Ber. 104, 3740 (1971).
7. U. Hasserodt and F. Korte, Angew. Chem. 75, 138 (1963).
8. C. Meier, Angew. Chem. Internat. Ed. Engl. 32, 1704 (1993).
9. M. M. Baizer, Tetrahedron 40, 935 (1984).
10. T. Shono, Electroorganic Chemistry as a New Tool in Organic Synthesis, p. 154, Springer-Verlag, Berlin (1984).
11. M. Kimura, H. Miyahara, N. Moritani and Y. Sawaki, J. Org. Chem. 55, 3897 (1990).
12. S. Torii, H. Kawafuchi and T. Inokuchi. Bull. Chem. Soc. Jpn 63, 2430 (1990).
13. M. Kimura, T. Yamashita, T. Kurata and Y. Sawaki, J. Chem. Soc., Chem. Commun. 259 (1990).
14. M. Kimura, H. Yamagishi and Y. Sawaki, Denki Kagaku 62, 1119 (1994).
15. M. Kimura, T. Kurata and Y. Sawaki, Recent Advances in Electroorganic Synthesis (Edited by S. Torii), p. 269, Kodansha, Tokyo (1987).
16. V. S. Abramov, Zh. Obshch. Khim. 22, 647 (1952); Chem. Abstr. 47, 5351h (1953).
17. V. S. Abramov, Zh. Obshch. Khim. 22, 647 (1952); Chem. Abstr. 47, 5351h (1953).
18. A. Zwierzak, Synthesis 305 (1976).
19. T. Fuchigami, T. Awata, T. Nonaka and M. M. Baizer, Bull. Chem. Soc. Jpn 59, 2873 (1986).
20. A. N. Pudovik and J. P. Kitanev, Zh. Obshch. Khim. 22, 467 (1952); Chem. Abstr. 47, 2685f (1953).
21. A. N. Pudovik and J. P. Kitanev, Zh. Obshch. Khim. 22, 467 (1952); Chem. Abstr. 47, 2685f (1953).
22. A. N. Pudovik and B. A. Arbuzov, Doklady Akad. Nauk. SSSR 73, 327 (1950); Chem. Abstr. 45, 2853a (1951).
23. A. N. Pudovik and B. A. Arbuzov, Doklady Akad. Nauk. SSSR 73, 327 (1950); Chem. Abstr. 45, 2853a (1951).
24. B. R. Rani, M. Ubukata and H. Osada, Bull. Chem. Soc. Jpn 68, 282 (1995).
25. M. S. Kharasch, R. M. Mosher and I. S. Bengelsdorf, J. Org. Chem. 25, 1000 (1960).
26. T. Shono, S. Kashimura and H. Nogusa, Chem. Lett. 425 (1986).
27. A. F. Janzen and T. G. Smyrl, Can. J. Chem. 50, 1205 (1972).
28. A. G. Brook, Acc. Chem. Res. 7, 77 (1974).
29. Y. Watanabe, E. Inada, M. Jinno and S. Ozaki, Tetrahedron Lett. 34, 497 (1993).
30. H. Ohmori, S. Nakai, M. Sekiguchi and M. Masui, Chem. Pharm. Bull. 27, 1700 (1979).
31. H. Goldwhite and B. C. Saunders, J. Chem. Soc. 2409 (1957).
32. V. S. Abramov, R. V. Dmitrieva and A. S. Kapustina, Zh. Obshch. Khim. 23, 257 (1953); Chem. Abstr. 48, 2572c (1954).
33. V. S. Abramov, R. V. Dmitrieva and A. S. Kapustina, Zh. Obshch. Khim. 23, 257 (1953); Chem. Abstr. 48, 2572c (1954).
34. J. Cheymol, P. Chabrier, M. Selim and P. Leduc, Compt. rend. 247, 1014 (1958).
35. T. Maeda, H. Abe, K. Kariki and T. Misato, Agr. Biol. Chem. 34, 700 (1970).
36. T. M. Chapman and D. G. Kleid, J. Org. Chem. 38, 250 (1973).
37. S.-I. Murahashi, Y. Taniguchi, Y. Imada and Y. Tanigawa, J. Org. Chem. 54, 3292 (1989).
38. K. Green, Tetrahedron Lett. 30, 4807 (1989).