Towards a correlation of absolute configuration and chiroptical properties of alkyl aryl sulfoxides: A coupled-oscillator foundation of the empirical Mislow rule?

Chemistry - A European Journal

Volumn 7, Issue 1, 2001, Pages 72-79

  Rosini, Carlo ^a   Donnoli, Maria Irene ^a   Superchi, Stefano ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

Asymmetric synthesis; Circular dichroism; Configuration determination; Conformation analysis; Sulfoxides

Indexed keywords

ALKYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFOXIDE;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; CIRCULAR DICHROISM; DRUG CONFORMATION; OPTICAL ROTATION; OSCILLATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0035808298     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010105)7:1<72::AID-CHEM72>3.0.CO;2-1     Document Type: Article

References (90)

1. a) P. Pitchen, Chem. Ind. 1994, 636;
2. b) M. Tanaka, H. Yamazaki, H. Hakasui, N. Nakamichi, H. Sekino, Chirality 1997, 9, 17;
3. c) S. von Unge, V. Langer, L. Sjölin, Tetrahedron: Asymmetry 1997, 8, 1967;
4. d) H. L. Holland, F. M. Brown, B. G. Larsen, Tetrahedron: Asymmetry 1994, 5, 1129;
5. e) C. A. Hutton, J. M. White, Tetrahedron Lett. 1997, 38, 1643;
6. f) S. Morita, J. Matsubara, K. Otsubo, K. Kitano, T. Ohtani, Y. Kawano, M. Uchida, Tetrahedron: Asymmetry 1997, 8, 3707;
7. g) H. L. Holland, F. M. Brown, Tetrahedron: Asymmetry 1998, 9, 535;
8. h) T. Nishi, K. Nakajima, Y. Iio, K. Ishibashi, T. Fukurawa, Tetrahedron: Asymmetry 1998, 9, 2567.
9. a) M. C. Carreño, Chem. Rev. 1995, 95, 1717;
10. b) G. Solladié, Synthesis 1981, 185;
11. c) K. K. Andersen in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), Wiley, Chichester, 1988, Chapter 3, pp. 53-94;
12. d) G. H. Posner in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), Wiley, Chichester, 1988, Chapter 16, pp. 823-849;
13. e) F. Colobert, A. Tito, N. Khiar, D. Denni, M. A. Medina, M. Martin-Lomas, J. L. G. Ruano, G. Solladiè, J. Org. Chem. 1998, 63, 8918;
14. f) P. Bravo, M. Crucianelli, A. Farina, S. V. Meille, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 1998, 435.
15. a) K. Hiroi, Y. Suzuki, Tetrahedron Lett., 1998, 39, 6499;
16. b) R. Tokuyo, M. Sodeska, L. Aol, Tetrahedron Lett. 1995, 36, 8035;
17. c) N. Khior, I. Fernandez, F. Alcudia, Tetrahedron Lett. 1993, 34, 123.
18. a) K. Mislow, A. L. Ternay, Jr., J. T. Melillo, J. Am. Chem. Soc. 1963, 85, 2329;
19. b) K. Mislow, M. M. Green, P. Laur, J.T. Melillo, T. Simmons, A. L. Ternay, Jr., J. Am. Chem. Soc. 1965, 87, 1958;
20. c) J. Jacobus, K. Mislow, J. Am. Chem. Soc. 1967, 89, 5228;
21. d) F. D. Saeva, D. R. Rayner, K. Mislow, J. Am. Chem. Soc. 1968, 90, 4176.
22. a) G. L. Bendazzoli, P. Palmieri, G. Gottarelli, I. Moretti, G. Torre, J. Am. Chem. Soc. 1976, 98, 2659;
23. b) I. Moretti, G. Torre, G. Gottarelli, Tetrahedron Lett. 1976, 711;
24. c) G. L. Bendazzoli, P. Palmieri, G. Gottarelli, I. Moretti, G. Torre, G. Gazz. Chim. Ital. 1979, 109, 19.
25. a) T. Sagae, S. Ogawa, N. Furukawa, Bull. Chem. Soc. Jpn. 1991, 64, 3179;
26. b) R. W. Baker, G. K. Thomas, D. S. Ren, M. V. Sargent, Aust. J. Chem. 1997, 50, 1151.
27. M. I. Donnoli, S. Superchi, C. Rosini, Enantiomer, 2000, 5, 181.
28. J. Gawronski in Methoden Org. Chem. (Houben-Weyl) 4th ed., 1995, Vol. 1, Chapter 4.4, p. 499.
29. a) S. Superchi, C. Rosini, Tetrahedron: Asymmetry 1997, 8, 349;
30. b) S. Superchi, M. I. Donnoli, C. Rosini, Tetrahedron Lett. 1998, 39, 8541;
31. c) M. I. Donnoli, S. Superchi, C. Rosini, J. Org. Chem. 1998, 63, 9392.
32. a) J.-M. Brunel, P. Diter, M. Duetsch, H. B. Kagan, J. Org. Chem. 1995, 60, 8086;
33. b) P. Pitchen, E. Duñach, M. N. Deshmukh, H. B. Kagan, J. Am. Chem. Soc. 1984, 106, 8188;
34. c) H. Sakuraba, K. Natori, Y. Tanaka, J. Org. Chem. 1991, 56, 4124;
35. d) T. Sugimoto, T. Kokubo, J. Miyazaki, S. Tanimoto, M. Okano, J. Chem. Soc. Chem. Commun. 1979, 402.
36. J. Murrel in The Theory of Electronic Spectra of Organic Molecules, Methuen, London, 1963, Chapter 10.
37. a) H. H. Jaffe, M. Orchin in The Theory and Application of UV Spectroscopy, Wiley, New York (USA), 1962;
38. b) S. Suzuki, T. Fujii, H. Baba, J. Mol Spectrosc. 1979, 47, 243.
39. See ref. [12a] pp. 480-481.
40. It is interesting that, on the basis of IR studies, it was shown that the MeSO group acts as a net resonance donor (N. C. Coutress, T. B. Grindley, A. R. Katritsky, R. D. Topsom, J. Chem. Soc. Perkin II 1974, 263); however, the above interpretation was found inconsistent with the NMR findings of Buchanan et al. (G. W. Buchanan, C. Rayes-Zamora, D. E. Clarke, Can. J. Chem. 1974, 52, 3895).
41. It is interesting that, on the basis of IR studies, it was shown that the MeSO group acts as a net resonance donor (N. C. Coutress, T. B. Grindley, A. R. Katritsky, R. D. Topsom, J. Chem. Soc. Perkin II 1974, 263); however, the above interpretation was found inconsistent with the NMR findings of Buchanan et al. (G. W. Buchanan, C. Rayes-Zamora, D. E. Clarke, Can. J. Chem. 1974, 52, 3895).
42. It should be noted that the structure of Scheme 2 (left) is slightly different from the most stable conformation of phenyl methyl sulfoxide found by Benassi (R. Benassi, U. Folli, D. Iarossi, A. Mucci, L. Schenetti, F. Taddei, J. Chem. Soc. Perkin Trans 2 1989, 517; R. Benassi, A. Mucci, L. Schenetti, F. Taddei, J. Mol. Struct. 1989, 184, 281), in which the S=O bond is almost coplanar with the phenyl ring.
43. It should be noted that the structure of Scheme 2 (left) is slightly different from the most stable conformation of phenyl methyl sulfoxide found by Benassi (R. Benassi, U. Folli, D. Iarossi, A. Mucci, L. Schenetti, F. Taddei, J. Chem. Soc. Perkin Trans 2 1989, 517; R. Benassi, A. Mucci, L. Schenetti, F. Taddei, J. Mol. Struct. 1989, 184, 281), in which the S=O bond is almost coplanar with the phenyl ring.
44. D. Casarini, E. Foresti, F. Gasparrini, L. Lunazzi, D. Macciantelli, D. Misiti, C. Villani, J. Org. Chem. 1993, 58, 5674.
45. W. H. Pirkle, C. J. Welch, M. M. Hyun, J. Org. Chem. 1983, 48, 5022.
46. R. W. Baker, D. C. R. Hockless, G. R. Pocok, M. V. Sargent, B. W. Skelton, A. N. Sobolev, E. Twiss (née Stanojevic), A. M. White, J. Chem. Soc. Perkin Trans. 1 1995, 2615.
47. It is noteworthy that the conformation of Sceme 2 (right) is very similar to the most stable structure of o-substituted phenyl methyl sulfoxides (see ref. [15]).
48. L. F. Tietze, A. Schuffenhauer, P. R. Schreiner, J. Am. Chem. Soc. 1998,120, 7952.
49. Treatments of the coupled-oscillator model and its application to organic stereochemistry: a) S. F. Mason, Quart. Rev. 1962, 17, 20;
50. b) "Theory II", S. F. Mason, in Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry (Ed.: G. Snatzke), Wiley, London, 1967, Chapter 4, p. 71;
51. c) G. Gottarelli, S. F. Mason, G. Torre, J. Chem. Soc. B 1971, 1349;
52. d) E. Charney in The Molecular Basis of Optical Activity - Optical Rotatory Dispersion and Circular Dichroism, Wiley, New York, 1979;
53. e) S. F. Mason, Molecular Optical Activity and Chiral Discrimination, Cambridge University Press, Cambridge, 1982.
54. a) N. Harada, K. Nakanishi, Acc. Chem. Res. 1972, 5, 257;
55. b) N. Harada, K. Nakanishi in Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, CA, 1983;
56. c) K. Nakanishi, N. Berova, in Circular Dichroism: Principles and Applications (Eds. K. Nakanishi, N. Berova, R. W. Woody), VCH, New York, 1994, Chapter 13, p. 361.
57. a) H. DeVoe, J. Chem. Phys. 1964, 41, 393;
58. b) H. DeVoe, J. Chem. Phys. 1965, 43, 3199.
59. -1. This expression gives rise to a couplet-like feature if the absorption maxima of chromophores 1 and 2 are close in frequency ("quasi-degenerate" coupled-oscillator system).
60. a) M. Zandomeneghi, J. Chem. Phys. 1979, 83, 2926;
61. b) M. Zandomeneghi, C. Rosini, A. F. Drake, J. Chem. Soc. Faraday Trans. 2 1981, 77, 567;
62. c) C. Rosini, M. Zandomeneghi, Gazz. Chim. Ital. 1981, 111, 493;
63. d) P. Salvadori, C. Bertucci, C. Rosini, M. Zandomeneghi, G. Gallo, E. Martinelli, P. Ferrari, J. Am. Chem Soc. 1981, 103, 5553;
64. e) C. Rosini, G. Giacomelli, P. Salvadori, J. Org. Chem. 1984, 49, 3394;
65. f) C. Rosini, C. Bertucci, P. Salvadori, M. Zandomeneghi, J. Am. Chem. Soc. 1985, 107, 17;
66. g) A. M. Caporusso, C. Rosini, L. Lardicci, C. Polizzi, P. Salvadori, Gazz. Chim. Ital. 1986,116, 467;
67. h) W. H. Pirkle, T. J. Sowin, P. Salvadori, C. Rosini, J. Org. Chem. 1988, 53, 826;
68. i) M. Clericuzio, C. Rosini, M. Persico, P. Salvadori, J. Org. Chem. 1991, 56, 4343;
69. j) C. Rosini, L. Franzini, P. Salvadori, G. P. Spada, J. Org. Chem. 1992, 57, 6820;
70. k) C. Rosini, P. Salvadori, M. Zandomeneghi, Tetrahedron: Asymmetry 1993, 4, 545;
71. l) G. Gottarelli, G. Proni, G. P. Spada, D. Fabbri, S. Gladiali, C. Rosini, J. Org. Chem. 1996, 61, 2013;
72. m) C. Rosini, R. Tanturli, P. Pertici, P. Salvadori, Tetrahedron: Asymmetry 1996, 7, 2971;
73. n) C. Rosini, G.P. Spada, G. Proni, S. Masiero, S. Scamuzzi, J. Am. Chem. Soc. 1997, 119, 506;
74. o) C. Rosini, R. Ruzziconi, S. Superchi, F. Fringuelli, O. Piermatti, Tetrahedron: Asymmetry 1998, 9, 55;
75. p) C. Rosini, C. Bertucci, C. Botteghi, R. Magarotto, Enantiomer, 1998, 3, 365.;
76. q) C. Rosini, S. Superchi, H. W. I. Peerlings, E. W. Meijer, Eur. J. Org. Chem. 2000, 61.
77. a) W. Hug, F. Ciardelli, I. Tinoco, J. Am. Chem. Soc. 1974, 96, 3407;
78. b) F. Ciardelli, C. Righini, M. Zandomeneghi, W. Hug, J. Phys. Chem. 1977, 81, 1948;
79. c) C. Bertucci, C. Carlini, F. Ciardelli, C. Rosini, P. Salvadori, Polym. Bull. 1981,5, 535;
80. d) J. Applequist, K. R. Sundberg, M. L. Olson, L. C. Weiss, J. Chem. Phys. 1979, 70, 1240;
81. e) K. A. Bode, J. Applequist, J. Phys. Chem. 1996, 100, 17825;
82. f) J. Applequist, K. A. Bode, J. Phys. Chem. B 1999, 103, 9767.
83. a) M. Zandomeneghi, C. Rosini, P. Salvadori, Chem. Phys. Lett. 1976, 44, 533;
84. b) C. Rosini, M. Zandomeneghi, P. Salvadori, J. Chem. Soc. Dalton Trans. 1978, 822.
85. J. A. Schellman, Acc. Chem. Res. 1968, 1, 194.
86. A. Rauk, H. A. Peoples, J. Comput. Chem. 1980, 1, 240.
87. See ref. [22b] pp. 194-195.
88. One could argue that 1-12, 15, and 16 should be considered as intrinsically dissymmetric chromophores, requiring an MO treatment. We intend to begin such a type of analysis.
89. H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
90. P. Lupattelli, R. Ruzziconi, P. Scafato, A. Degl'Innocenti, A. Belli Paolobelli, Synth. Commun. 1997, 27, 441.