An intramolecular Arbuzov rearrangement initiated by anodic oxidation

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1625-1628

  Yasui, Shinro ^a   Shioji, Kosei ^b   Tsujimoto, Munekazu ^a   Ohno, Atsuyoshi ^b  

^a TEZUKAYAMA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND;

ARTICLE; ELECTROCHEMISTRY; OXIDATION; REACTION ANALYSIS;

EID: 0029986879     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00072-X     Document Type: Article

References (14)

1. Engel, R. Synthesis of Carbon-Phosphorus Bonds, CRC Press, Boca Raton, FL, 1988; pp. 21 - 64.
2. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 87, 415 - 430.
3. This type of phosphonate is important as a precursor of the Honor-Emmons reaction. Mundy, B. P.; Ellerd, M. G. Name Reactions and Reagents in Organic Synthesis, John Wiley & Sons: New York, 1988; pp. 114 - 115.
4. Mullah, K. B.; Bentrude, W. G. J. Org. Chem. 1991, 56, 7218 - 7224.
5. (a) Omelanzcuk, J.; Sopchik, A. E., Lee, S.-G.; Akutagawa, K.; Cairns, S. M.; Bentrude, W. G. J. Am. Chem. Soc. 1988, 110, 6908 - 6909.
6. (b) Koptyug, I. V.; Ghatlia, N. D.; Sluggett, G. W.; Turro, N. J.; Ganapathy, S.; Bentrude, W. G. J. Am. Chem. Soc 1995, 117, 9486 - 9491.
7. (a) Yasui, S.; Fujii, M.; Kawano, C.; Nishimura, Y.; Shioji, K.; Ohno, A. J. Chem. Soc., Perkin Trans. 2 1994, 177 - 183.
8. (b) Yasui, S.; Shioji, K.; Ohno, A.; Yoshihara, M. J. Org. Chem. 1995, 60, 2099 -2105.
9. (c) Yasui, S.; Shioji, K.; Tsujimoto, M.; Ohno, A. Chem. Lett. 1995, 783 - 784.
10. It should be noted that the oxidation of 1b to 3b in methanol requires a stoichiometric quantity of electricity.
11. (a) Nakatani, S.; Yoshida, J.; Isoe, S. Tetrahedron 1993, 49, 2011 - 2024.
12. (b) Yoshida, J.; Nakatani, S.; Isoe, S. J. Org. Chem. 1993, 58, 4855 - 4865.
13. Watts, G. B.; Ingold, K. U. J. Am. Chem. Soc. 1972, 94, 2528 - 2529.
14. Bentrude, W. G. Acc. Chem. Res. 1982, 75, 117 - 125.