Reaction of an oxaruthenacycle with DMAD. Stoichiometric transformations of 2,6-xylenol to allylic phenols and benzopyrans via sp3 C-H bond cleavage reaction

Dalton Transactions

Volumn , Issue 17, 2009, Pages 3270-3279

  Hirano, Masafumi ^a   Izhab, Izirwan Bin ^a   Kurata, Naoki ^a   Koizumi, Kaori ^a   Komine, Nobuyuki ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGOSTIC INTERACTIONS; BENZOPYRANS; BENZYLIC; C-H BOND CLEAVAGES; DIMETHYL ACETYLENEDICARBOXYLATE; FLUXIONALITY; SHIFT REACTIONS; TOLUENE SOLUTIONS; VARIABLE-TEMPERATURE NMR; XYLENOL;

HEATING; MOLECULAR STRUCTURE; PHENOLS; ROTATION; RUTHENIUM; TOLUENE; X RAY ANALYSIS;

BIOLOGICAL MATERIALS;

EID: 64549110247     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b821179e     Document Type: Article

References (45)

1. A. S. Goldman, and K. I. Goldberg, in Activation and Functionalization of C-H Bonds, ACS symposium series, 885, American Chemical Society, Washington, DC, 2004
2. S. Murai, in Activation of Unreactive Bonds and Organic Synthesis, Springer, Berlin, 1999
3. B. A. Arndtsen R. G. Bergman T. A. Mobley T. H. Peterson Acc. Chem. Res 1995 28 154
4. R. H. Crabtree Chem. Rev 1985 85 254
5. E. Shilov A. A. Shteinman Coord. Chem. Rev 1977 24 97
6. J. Chatt J. M. Davidson J. Chem. Soc. 1965 843
7. D. Rabinovich R. Zelman G. Parkin J. Am. Chem. Soc. 1990 112 9632
8. D. Rabinovich R. Zelman G. Parkin J. Am. Chem. Soc. 1992 114 4611
9. T. Hascall V. J. Murphy G. Parkin Organometallics 1996 15 3910
10. W. D. Jones W. P. Kosar J. Am. Chem. Soc. 1986 108 5640
11. G. C. Hsu W. P. Kosar W. D. Jones Organometallics 1994 13 385
12. M. Hirano N. Kurata T. Marumo S. Komiya Organometallics 1998 17 501
13. M. Hirano N. Kurata S. Komiya J. Organomet. Chem. 2000 607 18
14. S. Komiya M. Hirano J. Chem. Soc. Dalton Trans. 2003 1439
15. M. Hirano Y. Sakaguchi T. Yajima N. Kurata N. Komine S. Komiya Organometallics 2005 24 4799
16. M. Hirano H. Sato N. Kurata N. Komine S. Komiya Organometallics 2007 26 2005
17. V. Ritleng C. Sirlin M. Pfeffer Chem. Rev. 2002 102 1731
18. J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, in Principles and Applications of Organotransition Metal Chemistry, University Science, 1982, p. 130
19. P. Dani M. A. M. Toorneman G. P. M. von Klink G. van Koten Organometallics 2000 19 5287
20. A. J. Toner S. Gründemann E. Clot H.-H. Limbach B. Donnadieu S. Sabo-Etienne B. Chaudret J. Am. Chem. Soc. 2000 122 6777
21. Y. Takahashi S. Hikichi M. Akita Y. Moro-oka Organometallics 1999 18 2571
22. A. R. Cowley J. R. Dilworth C. A. M. von Beckh W. Acta Crystal. Sec. E 2005 61 m1237
23. R.-M. Catala D. Cruz-Garritz P. Terreros H. Torrens A. Hills D. L. Hughes R. L. Richards J. Organomet. Chem. 1987 328 C37
24. R.-M. Catala D. Cruz-Garritz P. Terreros H. Torrens A. Hills D. L. Hughes R. L. Richards J. Organomet. Chem. 1989 359 219
25. M. Okazaki N. Yamahira J. J. G. Minglana T. Komuro H. Ogino H. Tobita Organometallics 2008 27 918
26. A. Yamamoto, in Organotransition Metal Chemistry, Fundamental Concepts and Application, Wiley, New York, 1986, p. 179
27. M. Brookhart M. L. H. Green J. Organomet. Chem. 1983 250 395
28. R. Ugi D. Marquading K. Klusacek P. Gillespie F. Ramirez Acc. Chem. Res. 1971 4 288
29. M. Miura T. Tsuda T. Satoh M. Nomura Chem. Lett. 1997 1103
30. M. I. Bruce, in Comprehensive Organometallic Chemistry, ed., G. Wilkinson, F. G. A. Stone, E. W. Abel, Pergamon, Oxford, 1982, Vol. 4, p 651
31. G. Mann D. Baranano J. F. Hartwig A. L. Rheingold I. A. Guzei J. Am. Chem. Soc. 1998 120 9205
32. M. S. Driver J. F. Hartwig J. Am. Chem. Soc. 1997 119 8332
33. G. Mann J. F. Hartwig J. Am. Chem. Soc. 1996 118 13109
34. D. Baranano J. F. Hartwig J. Am. Chem. Soc. 1995 117 2937
35. R. A. Widenhoefer S. L. Buchwald J. Am. Chem. Soc. 1998 120 6504
36. R. A. Widenhoefer H. A. Zhong S. L. Buchwald J. Am. Chem. Soc. 1997 119 6787
37. H. C. L. Abbenhuis M. Pfeffer J.-P. Sutter A. de Cian J. Fischer H. L. Ji J. H. Nelson Organometallics 1993 12 4464
38. W. Ferstl I. K. Sakodinskaya N. Beydoun-Sutter G. Le Borgne M. Pfeffer A. D. Ryabov Organometallics 1997 16 411
39. W. E. Parthan L. D. Huestis J. Am. Chem. Soc 1962 84 813
40. K. Anderson E. J. Lavoie J. Org. Chem. 1973 22 3832
41. G. M. Kosolapoff and L. Maier, in Organic Phosphorus Compounds, Wiley, New York, 1972, Vol. 1, p. 32
42. G. M. Sheldrick, SHELXL97, A program for Crystal Structure Refinement, University of Göttingen, Germany, 1997
43. H. D. Flack Acta Cryst. 1983 A39 876
44. M. J. Burn R. G. Bergman J. Organomet. Chem. 1994 472 43
45. K. Osakada K. Ohshiro A. Yamamoto Organometallics 1991 10 404