Superacid-Catalyzed Reductive Friedel-Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 151-156

  Fukuzawa, Shin Ichi ^a   Tsuchimoto, Teruhisa ^b   Hiyama, Tamejiro ^b  

^a CHUO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001632758     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961897e     Document Type: Article

References (22)

1. Roberts, R. M.; El-Khawaga, A. M.; Sweeney, K. M.; El-Zohry, M. F. J. Org. Chem. 1987, 52, 1591.
2. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081.
3. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. J. Am. Chem. Soc. 1995, 117, 11211.
4. TFSA is defined as the superacid by Olah et al. See: Olah, G. A.; Prakash, G. K. S.; Sommer, J. Science 1979, 206, 13.
5. Hashimoto, Y.; Hirata, K.; Kagoshima, H.; Kihara, N.; Hasegwa, M, Saigo, K. Tetrahedron 1993, 27, 5969; Tetrahedron Lett. 1992, 42, 6351.
6. Hashimoto, Y.; Hirata, K.; Kagoshima, H.; Kihara, N.; Hasegwa, M, Saigo, K. Tetrahedron 1993, 27, 5969; Tetrahedron Lett. 1992, 42, 6351.
7. Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
8. When the reaction was performed under Olah's conditions, i.e., adding 100 equiv of TFSA to the acetal, the reaction product was a complex mixture of compounds including diphenylmethane, triphenyl-methanol, triphenylmethane, anthracene, etc.
9. Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. J. Chem. Soc., Chem. Commun. 1996, 2345.
10. (a) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448.
11. (b) Olah, G. A.; Olah, J. A.; Ohyama, T. J. Am. Chem. Soc. 1984, 106, 5284.
12. (a) DeHaan, F. P.; Delker, G. L.; Covey, W. D.; Ahn, J.; Anksman, M. S.; Brehm, E. C.; Chang, J.; Chicz, R. M.; Cowan, R. L.; Ferrara, D. M.; Fong, C. H.; Harper, J. D.; Irani, C. D.; Kim, J. Y.; Meinhold, R. W.; Miller, K. D.; Roberts, M. P.; Stoler, E. M.; Suh, Y. J.; Tang, M.; Williams, E. L. J. Am. Chem. Soc. 1984, 106, 7038.
13. (b) DeHaan, F. P.; Chan, W. H.; Chang, J.; Cheng, T. B.; Chiriboga, D. A.; Irving, M. M.; Kaufman, C. R.; Kim, G. Y.; Kumar, A.; Na, J.; Nguyen, T. T.; Nguyen, D. T.; Patel, B. R.; Sarin, N. P.; Tidwell, J. H. J. Am. Chem. Soc. 1990, 112, 356.
14. Styrene dimer was one of the main products.
15. For a review, see: Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. 2, Part 1.
16. In the acid-catalyzed Friedel-Crafts reaction with benzaldehyde, the methyne hydrogen of triphenylmethane transfers to the benzyl cation to give diphenylmethane and the trityl cation, which is attacked by water. See ref 2.
17. Hydride ion transfer from the alkoxy carbon of tetrahydrofuran, 1,3-dioxolane, and 1,3-dioxepan to a trityl cation has been reported. Din, K-u.; Plesch, P. H. J. Chem. Soc., Perkin Trans. 2 1987, 937.
18. The oxidation product of the alkyl group was not detected because it may undergo a condensation reaction to form polymeric products.
19. 3 with a catalytic amount of TFSA similarly afforded diphenylmethane under the FC conditions, the terminal hydroxy group is not essential for the hydride shift process.
20. Roelofsen, D. P.; van Bekkum, H. Synthesis 1972, 419.
21. Napolitano, E.; Fiaschi, R.; Mastrorilli, E. Synthesis 1986, 122.
22. The general experimental protocols followed in this study parallel those described in the literature: Eliel, E. L.; Badding, V. D.; Rerick, M. N. J. Am. Chem. Soc. 1962, 84, 2371.