Superacid-catalyzed electrocyclization of 1-phenyl-2-propen-1-ones to 1- indanones. Kinetic and theoretical studies of electrocyclization of oxonium- carbenium dications

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6774-6780

  Suzuki, Takayoshi ^a   Ohwada, Tomohiko ^a   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BENZOPHENONE DERIVATIVE; FLUOROFORM; INDANONE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; PH;

EID: 0030816069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971100g     Document Type: Article

References (59)

1. Review: (a) Habermas, K.; Denmark, S. E. In Organic Reactions; Paquett, L. A., Ed.; John & Wiley & Sons, Inc.: New York, 1994; Vol. 45, Chapter 1, pp 1-158.
2. (b) Karstern, K. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 137-144.
3. (c) Denmark, S. In C"omprehensive Organic Synthesis; Trost, B., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, Chapter 6.3, pp 751-784.
4. (d) Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429-442.
5. (a) Shoppee, C. W.; Cooke, B. J. A. J. Chem. Soc., Perkin Trans. 1 1972, 2271-2276.
6. (b) Yates, P.; Yoda, N.; Brown, W.; Mann, B. J. Am. Chem. Soc. 1 1958, 80, 202-205.
7. Bladek, R.; Sorensen, T. S. Can. J. Chem. 1972, 50, 2806-2816.
8. Arnett E. M. Prog. Phys. Org. Chem. 1963, 1, 223-403.
9. Mayer, F.; Müller, P. Ber. Dtsch. Chem. Ges. 1927, 60, 2278-2283.
10. Dev, S. J. Indian Chem. Soc. 1957, 34, 169-177.
11. Braude, E. A.; Forbes, W. F. J. Chem. Soc. 1953, 2208-2216.
12. (a) Buruckhalter, J. H.; Fuson, R. C. J. Am. Chem. Soc. 1948, 70, 4184-4186
13. (b) Fuson, R. C.; Ross, W. E.; McKeever, C. H. J. Am. Chem. Soc. 1938, 60, 2935-2936.
14. (c) Matti, P. J.; Laval-Vergès, A.-M.; Emöd, I. Bull. Soc. Chim. Fr. 1963, 1176-1181.
15. deSolms, S. J.; Woltersdorf, O. W., Jr.; Cragoe, E. J., Jr.; Watson, L. S.; Fanelli, G. M. Jr. J. Med. Chem. 1978, 21, 437-443.
16. (a) Mannich, C; Heilner, G. Ber. Dtsch. Chem. Ges. 1922, 55, 356-365.
17. (b) Hansen, J. F.; Szymborski, P. A.; Vidusek, D. A. J. Org. Chem. 1979, 44, 661-662.
18. (c) Fiesselmann, H.; Ribka, J. Ber. Dtsch. Chem. Ges. 1956, 89, 27-39, 40-51.
19. Woodward, R. B.; Hoffmann, R. "The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970.
20. Ohwada, T.; Yamagata, N.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 1364-1373.
21. 0) of the trifluoromethanesulfonic acid (TFSA)-trifluoroacetic acid (TFA) system is described in Saito, S.; Saito, S.; Ohwada, T.; Shudo, K. Chem. Pharm. Bull. 1991, 39, 2718-2720. See also: Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317, footnote 8.
22. 0) of the trifluoromethanesulfonic acid (TFSA)-trifluoroacetic acid (TFA) system is described in Saito, S.; Saito, S.; Ohwada, T.; Shudo, K. Chem. Pharm. Bull. 1991, 39, 2718-2720. See also: Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317, footnote 8.
23. BH+ value of cyclopropanone (-7.5) to those of the enones and indanones (refs 4 and 15), its inert reactivity, and the absence of strong UV absorption.
24. (a) Paspaleev, E.; Kojucharova. Monatsch. Chem. 1969, 100, 1213-1221.
25. (b) Campbell, H. J.; Edward, J. T. Can. J. Chem. 1960, 38, 2109.
26. (c) Stewart, R.; Yates, K. J. Am. Chem. Soc. 1958, 80, 6355.
27. Zucker, L. Hammett, L. P. J. Am. Chem. Soc. 1939, 61, 2791-_ 2798. Bonner, T. G.; Thorne, M. P.; Wilkins, J. M. J. Chem. Soc. 1955, 2351-2358. Bonner, T. G.; Barnard, M. J. Chem. Soc. 1958, 4181-4186.
28. Zucker, L. Hammett, L. P. J. Am. Chem. Soc. 1939, 61, 2791-_ 2798. Bonner, T. G.; Thorne, M. P.; Wilkins, J. M. J. Chem. Soc. 1955, 2351-2358. Bonner, T. G.; Barnard, M. J. Chem. Soc. 1958, 4181-4186.
29. Zucker, L. Hammett, L. P. J. Am. Chem. Soc. 1939, 61, 2791-_ 2798. Bonner, T. G.; Thorne, M. P.; Wilkins, J. M. J. Chem. Soc. 1955, 2351-2358. Bonner, T. G.; Barnard, M. J. Chem. Soc. 1958, 4181-4186.
30. Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317.
31. Ohwada, T.; Yamazaki, T.; Suzuki, T.; Saito, S; Shudo, K. J. Am. Chem. Soc. 1996, 118, 6220-6224.
32. Fãrcasiu, D. Ghenciu, A. J. Org. Chem. 1991, 56, 6050-6052.
33. Blackburn, C.; Childs, R. F. J. Chem. Soc., Chem. Commun. 1984, 812-813.
34. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S., J. Am. Chem. Soc. 1995, 117, 11211-11214. See for a general reference of superelectrophiles: Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767-788.
35. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S., J. Am. Chem. Soc. 1995, 117, 11211-11214. See for a general reference of superelectrophiles: Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767-788.
36. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081-11084.
37. -1, respectively (see Table 3).
38. Gaussian 94, Revision B.2: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowsfi, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
39. Breulet, J.; Schaefer, H. F., III. J. Am. Chem. Soc. 1984, 106, 1221-1226. Houk, K. N.; Li, Y.; Evanseck, J. D. AngeW. Chem., Int. Ed. Engl. 1991, 31, 682-708. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc., 1985, 107, 2099-2111.
40. Breulet, J.; Schaefer, H. F., III. J. Am. Chem. Soc. 1984, 106, 1221-1226. Houk, K. N.; Li, Y.; Evanseck, J. D. AngeW. Chem., Int. Ed. Engl. 1991, 31, 682-708. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc., 1985, 107, 2099-2111.
41. Breulet, J.; Schaefer, H. F., III. J. Am. Chem. Soc. 1984, 106, 1221-1226. Houk, K. N.; Li, Y.; Evanseck, J. D. AngeW. Chem., Int. Ed. Engl. 1991, 31, 682-708. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc., 1985, 107, 2099-2111.
42. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. (b) Lee, C.; Yang, W.; Parr, R. G. PhyS. Rev. B 1988, 37, 785.
44. (c) Bauschlicher, Jr.; Paartridge, H. J. Chem. Phys. 1995, 103, 1788.
45. (d) Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian Inc.: Pittsburgh, 1993.
46. A superior description of transition structures of concerted Diels-Alder cyclizations in terms of density-functional theories rather than MP electron correlations was discussed in Goldstein, E.; Beno, B., Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043
47. Smith, D. A.; Ulmer, C. W., II. Tetrahedron Lett. 1991, 32, 725-728.
48. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
49. (b) Pople, J. A.; Scott, A. P.: Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 345-350.
50. (c) Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley and Sons, Inc.: New York, 1986.
51. The s-cis structure 11b is also favored in the neutral 1-pnenyl-2-propenone 11 over the s-trans isomer 11a (1.34 kcal/mol, HF/6-31*, data not shown).
52. (a) Schleyer, P. von R.; Bentley, T. W.; Koch, W.; Kos, A. J.; Schwarz, H. J. Am. Chem. Soc. 1987, 109, 6953-6957.
53. (b) Kallel, E. A.; Houk, K. N. J. Org. Chem. 1989, 54, 6006-6008.
54. (a) Deno, N. C.; Pittman, C. U., Jr.; Turner, J. O. J. Am. Chem. Soc. 1965, 87, 2153-2157.
55. (b) Olah, G. A.; Asensio, G.; Mayr, H. J. Org. Chem. 1978, 43, 1518-1520.
56. (c) Prakash, G. K. S.; Krishnamurthy, V. V.; Olah, G. A.; Farnum, D. G. J. Am. Chem. Soc. 1985, 107, 3928-3935. See also: Bergmann, F.; Israelashwili, S. J. Am. Chem. Soc. 1946, 68, 1-5.
57. (c) Prakash, G. K. S.; Krishnamurthy, V. V.; Olah, G. A.; Farnum, D. G. J. Am. Chem. Soc. 1985, 107, 3928-3935. See also: Bergmann, F.; Israelashwili, S. J. Am. Chem. Soc. 1946, 68, 1-5.
58. 2-substituent, would reduce the entropy change required for the cyclization.
59. Gassman, P. G.; Ray, J. A.; Wenthold, P. G.; Mickelson, J. N. J. Org. Chem. 1991, 56, 5143-5146.