Superacid-catalyzed reaction of substituted benzaldehydes with benzene

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8089-8093

  Saito, Shinichi ^a   Ohwada, Tomohiko ^a   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000268839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960665c     Document Type: Article

References (24)

1. Griepentrog, H. Ber. Dtsh. Chem. Ges. 1886, 19, 1876-1877. For review, see Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Wiley: New York, 1964: vol. II, Chapter XIX (Hofmann, J. E., Schriesheim, A.) pp 616-621.
2. Griepentrog, H. Ber. Dtsh. Chem. Ges. 1886, 19, 1876-1877. For review, see Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Wiley: New York, 1964: vol. II, Chapter XIX (Hofmann, J. E., Schriesheim, A.) pp 616-621.
3. Schaarschmidt, A.; Hermann, L.; Szemzo, B. Ber. Dtsh. Chem. Ges. 1925, 58, 1914-1916.
4. Hey, D. H. J. Chem. Soc. 1935, 72-75.
5. Ellison, H.; Hey, D. H. J. Chem. Soc. 1938, 1847-1853.
6. Ungnade, H. E.; Crandall, E. W. J. Am. Chem. Soc. 1949, 71, 2209-2210.
7. Ungnade, H. E.; Kline, E. F.; Crandall, E. W. J. Am. Chem. Soc. 1953, 75, 3333-3336.
8. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211-11214.
9. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081-11084.
10. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
11. Since 1 mol of 6 reacted with benzene to give 1 mol of 7 and a total of 1 mol of 3 plus 4 (0.5 mol each), the total yield would theoretically be 200%. The yields of the following reactions were also calculated similarly.
12. Transacetylation of acetylmesitylene has been reported. See, Keumi, T.; Monta, T.; Shimada, T.; Teshima, N.; Kitajima, H.; Prakash, G. K. S. J. Chem. Soc., Perkin Trans. 2 1986, 847-852.
13. The reversibility of Friedel-Crafts acylation has been reported by Agranat et al. See, Agranat, I.; Bentor, Y.; Shih, Y.-S. J. Am. Chem. Soc. 1977, 99, 7068-7070. Agranat, I.; Shih, Y.-S.; Bentor, Y. J. Am. Chem. Soc. 1974, 96, 1259-1260. Agranat, I.; Avnir, D. J. Chem. Soc., Chem. Commun. 1973, 362-363.
14. The reversibility of Friedel-Crafts acylation has been reported by Agranat et al. See, Agranat, I.; Bentor, Y.; Shih, Y.-S. J. Am. Chem. Soc. 1977, 99, 7068-7070. Agranat, I.; Shih, Y.-S.; Bentor, Y. J. Am. Chem. Soc. 1974, 96, 1259-1260. Agranat, I.; Avnir, D. J. Chem. Soc., Chem. Commun. 1973, 362-363.
15. The reversibility of Friedel-Crafts acylation has been reported by Agranat et al. See, Agranat, I.; Bentor, Y.; Shih, Y.-S. J. Am. Chem. Soc. 1977, 99, 7068-7070. Agranat, I.; Shih, Y.-S.; Bentor, Y. J. Am. Chem. Soc. 1974, 96, 1259-1260. Agranat, I.; Avnir, D. J. Chem. Soc., Chem. Commun. 1973, 362-363.
16. For recent examples, see Kim, E. K.; Lee, K. Y.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 1756-1770. Xiong, Y.; Rodewald, P. G.; Chang, C. D. J. Am. Chem. Soc. 1994, 116, 9427-9431.
17. For recent examples, see Kim, E. K.; Lee, K. Y.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 1756-1770. Xiong, Y.; Rodewald, P. G.; Chang, C. D. J. Am. Chem. Soc. 1994, 116, 9427-9431.
18. The importance of the use of the superacid catalyst TFSA was also demonstrated in the reactions of substituted benzaldehydes with benzene. The rate of the reaction decreased in the presence of less acidic catalysts such as 5-10% (w/w) TFSA-90-95% trifluoroacetic acid, which is acidic enough to monoprotonate the aldehydes. Though monoprotonated aldehydes may react slowly with benzene, the reactivity is greatly enhanced in the presence of TFSA. See also refs 7 and 8.
19. The formation of a small amount of 15 in the reaction of 4-(trifluoromethyl)benzaldehyde (13) with benzene could be explained by the solvolytic transformation of 14 to 4-(diphenylmethyl)benzen-ecarboxylic acid or its equivalent, followed by reaction with benzene. See also, Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317.
20. Saito, S.; Saito, S.; Ohwada, T.; Shudo, K. Chem. Pharm. Bull. 1991, 39(10), 2718-2720.
21. Lichtin, N. N.; Glazer, H. J. Am. Chem. Soc. 1951, 73, 5537-5541.
22. Gribble, G. W.; Leese, R. M.; Evans, B. E. Synthesis 1977, 172-176.
23. Schlenk, W.; Weickel, T.; Herzenstein, A. Justus Liebig Ann. Chem. 1910, 372, 1-20.
24. Zarkadis, A. K.; Neumann, W. P.; Uzick, W. Chem. Ber. 1985, 118, 1183-1192.