Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers

Tetrahedron

Volumn 63, Issue 46, 2007, Pages 11377-11385

  Taylor, Stephen R ^a   Ung, Alison T ^a   Pyne, Stephen G ^a   Skelton, Brian W ^b   White, Allan H ^b  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHOXYPHENYL 3,4 DIMETHOXYPHENYLACETATE; BIPHENYL; ETHER DERIVATIVE; LACTONE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PRIORITY JOURNAL; REPRODUCIBILITY; X RAY CRYSTALLOGRAPHY;

EID: 34848815633     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.082     Document Type: Article

References (38)

1. Jempty T.C., Gogins K.A.Z., Mazur Y., and Miller L.L. J. Org. Chem. 46 (1981) 4545-4551
2. Jempty T.C., Miller L.L., and Mazur Y. J. Org. Chem. 45 (1980) 749-751
3. Waldvogel S.R. Synlett (2002) 622-624
4. Kramer B., Frohlich R., Bergander K., and Waldvogel S.R. Synthesis 1 (2003) 91-96
5. Kumar S., and Manickam M. Chem. Commun. (1997) 1615-1616
6. Mirk D., Wibbeling B., Frohlich R., and Waldvogel S.R. Synlett (2004) 1970-1974
7. Waldvogel S.R., Aits E., Holst C., and Frohlich R. Chem. Commun. (2002) 1278-1279
8. Schwartz M.A., Rose B.F., Holton R.A., Scott S.W., and Vishnuvajjala B. J. Am. Chem. Soc. 99 (1977) 2571-2578
9. Elliot I.W. J. Org. Chem. 42 (1977) 1090-1093
10. Kupchan S.M., Liepa A.J., Kameswaran V., and Bryan R.F. J. Am. Chem. Soc. 95 (1973) 6861-6863
11. Damon R.E., Schlessinger R.H., and Blount J.F. J. Org. Chem. 41 (1976) 3772-3773
12. Kupchan S.M., Dhingra O.P., Kim C.-K., and Kameswaran V. J. Org. Chem. 41 (1976) 4047-4049
13. Kupchan S.M., Dhingra O.P., Kim C.-K., and Kameswaran V. J. Org. Chem. 43 (1978) 2521-2529
14. Kupchan S.M., Kameswaran V., Lynn J.T., Williams D.K., and Liepa A.J. J. Am. Chem. Soc. 97 (1975) 5622-5623
15. Morimoto T., Chiba M., and Achiwa K. Tetrahedron 49 (1993) 1793-1806
16. Kende A.S., Liebeskind L.S., Mills J.E., Rutledge P.S., and Curran D.P. J. Am. Chem. Soc. 99 (1977) 7082-7083
17. Evans D.A., Cain P.A., and Wong R.Y. J. Am. Chem. Soc. 99 (1977) 7083-7085
18. McKillop A., Turrell A.G., Young D.W., and Taylor E.C. J. Am. Chem. Soc. 102 (1980) 6504-6512
19. Taylor E.C., Andrade J.G., Rall G.J.H., and McKillop A. J. Am. Chem. Soc. 102 (1980) 6513-6519
20. Lau W., and Kochi J.K. J. Am. Chem. Soc. 106 (1984) 7100-7112
21. Norman R.O.C., Thomas C.B., and Ward P.J. J. Chem. Soc., Perkin Trans. 1 (1973) 2914-2917
22. Planchenault D., Dhal R., and Robin J.-P. Tetrahedron 49 (1993) 5823-5830
23. Tohma H., Morioka H., Takizawa S., Arisawa M., and Kita Y. Tetrahedron 57 (2001) 345-352
24. Arisawa M., Utsumi S., Nakajima M., Ramesh N.G., Tohma H., and Kita Y. Chem. Commun. (1999) 469-470
25. Kita Y., Takada T., Gyoten M., Tohma H., Zenk M.H., and Eichhorn J. J. Org. Chem. 61 (1996) 5857-5864
26. Hamamoto H., Anilkumar G., Tohma H., and Kita Y. Chem. Commun. (2002) 450-451
27. Tohma H., and Kita Y. Top. Curr. Chem. 224 (2003) 209-248
28. Olivera R., San Martin R., and Dominguez E. J. Org. Chem. 65 (2000) 7010-7019
29. Churruca F., San Martin R., Tellitu I., and Dominguez E. Eur. J. Org. Chem. (2005) 2481-2490
30. Moreno I., Tellitu I., Dominguez E., and San Martin R. Eur. J. Org. Chem. (2002) 2126-2135
31. Moreno I., Tellitu I., Etayo J., San Martin R., and Dominguez E. Tetrahedron 57 (2001) 5403-5411
32. Carbocycles have also been generated from bis(3,4-dimethoxyphenyl) alkanes phenyl ethers by electrochemical oxidation, see:. Ronlan A., and Parker V.D. J. Am. Chem. Soc. 39 (1974) 1014-1016
33. Hamamoto H., Anilkumar G., Tohma H., and Kita Y. Chem.-Eur. J. 8 (2002) 5377-5383
34. Takada T., Arisawa M., Gyoten M., Hamada R., Tohma H., and Kita Y. J. Org. Chem. 63 (1998) 7698-7706
35. The electrochemical oxidation of di-aryl esters has been shown to give in one case a diphenyl derivative from intermolecular coupling. Further oxidation of this compound gave a para-quinone product. Other esters gave oligomeric products, see:. Sainsbury M., and Wyatt J. J. Chem. Soc., Perkin Trans. 1 (1979) 108-114
36. In: Eliel E.L., and Wilen S.H. (Eds). Stereochemistry of Organic Compounds (1994), Wiley, New York, NY 618-620
37. Elliott I.W., Sloan M.J., and Tate E. Tetrahedron 52 (1996) 8063-8072
38. Cromartie R.I.T., Harley-Mason J., and Wannigama D.G.P. J. Chem. Soc. (1958) 1982-1985