Iron lewis acid catalyzed reactions of phenyldiazomethane with aromatic aldehydes

Tetrahedron

Volumn 54, Issue 3-4, 1998, Pages 349-358

  Mahmood, Syed J ^a   Saha, Anjan K ^a   Mahmun Hossain, M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DIAZOMETHANE; EPOXIDE; IRON; KETONE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRON TRANSPORT; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 0032518920     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10287-3     Document Type: Article

References (27)

1. 1. (a) Gutsche, C. D. Org. React. 1954, 8, 365.
2. (b) Cowell, G. W.; Ledwith, A. Q. Rev. 1970, 24, 119.
3. (c) Wulfmann, D. S.; Linstrumelle, G.; Cooper, C. F. in The Chemistry of Diazonium and Azo Groups, S. Patai, Ed., Interscience, New York, 1978, p 821.
4. (d) Hegarty, A. F. ibid. p 511.
5. (e) Regitz, M. ibid. p 659.
6. (f) Whittaker, D. ibid, p 593.
7. (g) Meth-Cohn, O.; Suschizky, H. Chem. Ind. 1969, 443.
8. (h) Methoden Org. Chem. (Houben-Weyl), 4th Ed., 1968, 10/4.
9. 2. Loeschorn, C. A.; Nakajima, M.; McCloskey, P. J.; Anselme, J-P. J. Org. Chem. 1983, 48, 4407.
10. 3. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
11. 4. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7090.
12. 5. Aggarwal, V. K.; Abdel-Rahman, H.; Jones, R. V. H.; Lee, H. Y.; Reid, B. D. J. Am. Chem. Soc. 1994, 116, 5973.
13. 6. Seitz, W. J.; Saha, A. K.; Hossain, M. M. Organometallics 1993, 12, 2604.
14. 7. King, R. B. J. Inorg. Nucl. Chem. 1963, 25, 1296.
15. 8. Imuta, M.; Ziffer, H. J. Org. Chem., 1979, 44, 2505.
16. 9. Loeschorn, C. A.; Nakajima, M.; Mc Closkey, P. J.; Anselme, J-P. J. Org Chem. 1983, 48, 4407.
17. 10. Phenyldiazomethane is known to decompose in the presence of metal Lewis acid to form cis/trans stilbenes and azine. (a) Sankar, B. K. R.; Shechter, H. Tetrahedron Lett. 1982, 23, 2277.
18. (b) Seitz, W. J.; Hossain, M. M. Tetrahedron Lett. 1994, 35, 7561.
19. 11. Blanco, F. E.; Harris, F. L. J. Org. Chem. 1977, 42, 868.
20. 12. Vargas, R. M.; Theys, R. D.; Hossain, M. M. J. Am. Chem. Soc. 1992, 114, 777.
21. 13. Cicero, Ronald L.; Protasiewicz, John D. Organometallics 1995, 14, 4792.
22. 14. (a)Maruoka, K.; Nagahara, S.; Ooi, T.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 5607.
23. (b) Miyashita, A.; Shimada, T.; Sugawara, A.; Nohira, H. Chemistry Lett. 1986, 1323.
24. 15. (a) Casey C. P.; Vosejpka , L. J. S. Organometallics 1992, 11, 738.
25. (b) Brookhart, M.; Liu, Y. J. Am. Chem. Soc. 1991, 113, 939 and also see ref. 6.
26. 16. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A, 3rd. ed., Plenum Press, New York, 1990, p 275 and 313.
27. 17. Creary, X. Org. Synthesis 1986, 64, 207.