[2+2]-cycloaddition reaction of styrene derivatives using an Fe(III) salt catalyst

Chemistry Letters

Volumn , Issue 7, 2001, Pages 624-625

  Ohara, Hiroyuki ^a   Itoh, Toshiyuki ^a   Nakamura, Masaharu ^b   Nakamura, Eiichi ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035613270     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.624     Document Type: Article

References (15)

1. A review see. P. Laszlo, Acc. Chem. Res., 19, 121 (1986).
2. H. Ohara, K. Kudo, T. Itoh, M. Nakamura, and E. Nakamura, Heterocycles, 52, 505 (2000).
3. A review see. a) N. L. Bauld, Tetrahedron, 45, 5307 (1989). Photodimerization:
4. b) K. Mizuno, C. Pac, and H. Sakurai, Chem. Lett., 1973, 309.
5. C. Pac, K. Mizuno, T. Sugioka, and H. Sakurai, Chem. Lett., 1973, 187.
6. C. Pac, T. Sugioka, K. Mizuno, and H. Sakurai, Bull. Chem. Soc. Jpn., 46, 238 (1973).
7. e) F. D. Lewis and M. Kojima, J. Am. Chem. Soc., 110, 8660 (1988). D F. D. Lewis and M. Kojima. J. Am. Chem. Soc., 110, 8664 (1988). Tris(p-bromophenyl)aminium hexachloroantimonate:
8. e) F. D. Lewis and M. Kojima, J. Am. Chem. Soc., 110, 8660 (1988). D F. D. Lewis and M. Kojima. J. Am. Chem. Soc., 110, 8664 (1988). Tris(p-bromophenyl)aminium hexachloroantimonate:
9. g) N. L. Bauld and R. Pabon, J. Am. Chem. Soc., 105, 633 (1983).
10. a) F. A. Bell, R. A. Crellin, and A. Ledwith, J. Chem. Soc., D, 1969, 251.
11. b) D. W. Reynolds, K. T. Lorenz, H-S. Chiou, D. J. Bellville, R. A. Pabon, and N. L. Bauld, J. Am. Chem. Soc., 109, 4960 (1987).
12. It was proposed that [2+2]-cycloaddition proceeds through an electron transfer (ET) pathway: a) for a review see: A. Ledwith, Acc. Chem. Res., 5, 133 (1972).
13. b) for the most recent example see: G. D. Reddy and O. Wiest, J. Org. Chem., 64, 2860 (1999).
14. 3) δ 157.9, 135.9, 127.7, 113.7, 55.2 52.4, 43.2, 18.9.
15. 3CN (0.5 mL) and the solvent was removed at 60 °C under reduced pressure using a rotary evaporator. The mixture was dried under vacuum and the resulting uniformly orange powder was used for the reaction. The catalyst should be handled with care because it has been reported that iron(III) perchlorate salt detonates with violence when subjected to mechanical or thermal shock. However, our catalyst is believed to be safe due to the support by neutral alumina. The content of Fe(III) ion was determined by iodometry titration in aqueous solution.