Geometric requirements for hydrogen abstractability and 1,4-biradical reactivity in the Norrish/Yang type II reaction: Studies based on the solid state photochemistry and X-ray crystallography of medium-sized ring and macrocyclic diketones

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6167-6184

  Gudmundsdottir, Anna D ^a   Lewis, Thillairaj J ^a   Randall, Leslie H ^a   Scheffer, John R ^a   Rettig, Steven J ^a   Trotter, James ^a   Wu, Chung Hsi ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030018947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953420a     Document Type: Article

References (81)

1. For a recent review of organic photochemistry in crystals and other organized media, see: Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991.
2. Portions of this work have appeared in preliminary communication form: (a) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1990, 112, 3679. (b) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1991, 113, 8180. (c) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. Mol. Cryst. Liq. Cryst. 1992, 219, 17.
3. Portions of this work have appeared in preliminary communication form: (a) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1990, 112, 3679. (b) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1991, 113, 8180. (c) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. Mol. Cryst. Liq. Cryst. 1992, 219, 17.
4. Portions of this work have appeared in preliminary communication form: (a) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1990, 112, 3679. (b) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1991, 113, 8180. (c) Lewis, T. J.; Rettig, S. J.; Scheffer, J. R.; Trotter, J. Mol. Cryst. Liq. Cryst. 1992, 219, 17.
5. Allinger, N. L.; Gorden, B. J.; Newton, M. G.; Lauritsen-Norskov, L.; Profeta, S., Jr. Tetrahedron 1982, 38, 2905.
6. Scheffer, J. R. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987; Chapter 1.
7. (a) Ruzicka, L.; Brugger, N.; Seidel, C. F.; Schinz, H. Helv. Chim. Acta 1928, 11, 496.
8. (b) Ruzicka, L.; Stoll, M.; Huyser, H. W.; Boekenoogen, H. A. Helv. Chim. Acta 1930, 13, 1152.
9. Alvik, T.; Borgen, G.; Dale, J. Acta Chem. Scand. 1972, 26, 1805.
10. Schulte-Elte, K. H.; Willhalm, B.; Thomas, A. F.; Stoll, M.; Ohloff, G. Helv. Chim. Acta 1971, 54, 1759.
11. Burchill, P. J.; Kelso, A. G.; Power, A. J. Aust. J. Chem. 1976, 29, 2477.
12. Matsui, K.; Mori, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1971, 44, 3440.
13. (a) Blomquist, A. T.; Spencer, R. D. J. Am. Chem. Soc. 1948, 70, 30.
14. (b) Blomquist, A. T.; Prager, J.; Wolinsky, J. J. Am. Chem. Soc. 1955, 77, 1804.
15. Cordonnier, G.; Sliwa, H. J. Hetereocycl. Chem. 1978, 24, 111.
16. Interestingly, treatment of adipyl chloride with triethylamine is reported to lead to a dimer of structure i (Baldwin, J. E. J. Org. Chem. 1963, 28, 3112), and treatment of this compound with aqueous sodium hydroxide was shown to lead to hydroxy-acid ii. On this basis, we tend to rule out a dimer analogous to i as being responsible for the formation of γ-pyrones 3b and 3c from suberyl and pimeloyl chloride, respectively. For a recent review on the subject of bisketenes and related compounds, see: Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D. Acc. Chem. Res. 1995, 28, 265. Equation Present
17. Interestingly, treatment of adipyl chloride with triethylamine is reported to lead to a dimer of structure i (Baldwin, J. E. J. Org. Chem. 1963, 28, 3112), and treatment of this compound with aqueous sodium hydroxide was shown to lead to hydroxy-acid ii. On this basis, we tend to rule out a dimer analogous to i as being responsible for the formation of γ-pyrones 3b and 3c from suberyl and pimeloyl chloride, respectively. For a recent review on the subject of bisketenes and related compounds, see: Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D. Acc. Chem. Res. 1995, 28, 265. Equation Present
18. Cyclobutanol products in type II photochemistry were first reported by: Yang, N. C.; Yang, D. H. J. Am. Chem. Soc. 1958, 80, 2913.
19. Wagner, P. J.; Kochevar, I. E.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7489.
20. Sauers, R. R.; Huang, S.-Y. Tetrahedron Lett. 1990, 31, 5709.
21. Bernard, M.; Yang, N. C. Proc. Chem. Soc. 1958, 302.
22. The crystallographic data for cyclobutanols 4d, 5f, 4j, and 4′j are compiled in Table 3.
23. Wagner, P. J. Acc. Chem. Res. 1972, 4, 168.
24. Fleming, I.; Long, W. E. J. Chem. Soc., Perkin Trans. 2 1976, 14.
25. (a) Coulson, D. R.; Yang, N. C. J. Am. Chem. Soc. 1966, 88, 4511.
26. (b) Yang, N. C.; Elliot, S. P. J. Am. Chem. Soc. 1969, 91, 7550.
27. Fleming, I.; Kemp-Jones, A. V.; Long. W. E.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 2 1976, 7.
28. Müller, A. Helv. Chim. Acta 1933, 16, 155. Cell constants: a = 9.91 Å, b = 8.13 Å, c = 30.79 Å, β = 68.5○.
29. Germain, G., personal communication as reported by: Dunitz, J. D. In Perspectives in Structural Chemistry; Dunitz, J. D., Ibers, J. A., Eds.; Wiley: New York, 1968; Vol. 2, p 495.
30. Bernstein, J. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987; Chapter 13, pp 471-518.
31. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000.
32. Fyfe, C. A. Solid State NMR for Chemists; C.F.C. Press: Guelph, Canada, 1983.
33. Turro, N. J. Modern Molecular Photochemistry; Benjamin-Cummings: Menlo Park, CA, 1978; Chapter 10.
34. Kasha, M. Radiat. Res. 1960, Suppl. 2, 243. See also: Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527.
35. Kasha, M. Radiat. Res. 1960, Suppl. 2, 243. See also: Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527.
36. Bondi, A. J. Phys. Chem. 1964, 68, 441. See also: Edward, J. T. J. Chem. Educ. 1970, 47, 261.
37. Bondi, A. J. Phys. Chem. 1964, 68, 441. See also: Edward, J. T. J. Chem. Educ. 1970, 47, 261.
38. Dorigo, A. E.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 2195 and references cited therein.
39. (a) Wagner, P.; Park, B-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4.
40. (b) Wagner, P. J. Top. Curr. Chem. 1976, 66, 1.
41. (c) Wagner, P. J.; Zhou, B.; Hasegawa, T.; Ward, D. L. J. Am. Chem. Soc. 1991, 113, 9640.
42. 40 on the triplet state geometries of aliphatic aldehydes and ketones support the picture of a partially (22-45○) pyramidalized carbonyl group.
43. 40 on the triplet state geometries of aliphatic aldehydes and ketones support the picture of a partially (22-45○) pyramidalized carbonyl group.
44. Chandler, W.; Goodman, L. J. Mol. Spectrosc. 1970, 35, 232.
45. Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; Zepp, R. G. J. Am. Chem. Soc. 1972, 94, 7500.
46. Scheffer, J. R.; Trotter, J.; Omkaram, N.; Evans, S. V.; Ariel, S. Mol. Cryst. Liq. Cryst. 1986, 134, 169.
47. Slivinskas, J. A.; Guillet, J. E. J. Polym. Sci., Polym. Chem. Ed. 1973, 11, 3043.
48. (a) Anet, F. A. L.; Cheng, A. K.; Krane, J. J. Am. Chem. Soc. 1973, 95, 7877.
49. (b) Since the 18-membered-ring diketone 1e does not have a rectangular conformation in the solid state, the β-carbon in this case is not strictly speaking a corner position. Nevertheless, Figure 6 depicts the situation accurately.
50. Sauers, R. R.; Krogh-Jespersen, K. Tetrahedron Lett. 1989, 30, 527.
51. 13C NMR spectrum, and based on our work (see section on characterization of photoproducts), this can be taken as indicating a cis ring junction.
52. Sauers, R. R.; Edberg, L. A. J. Org. Chem. 1994, 59, 7061.
53. Lewis, T. J.; Rettig, S. J.; Sauers, R. R.; Scheffer, J. R.; Trotter J.; Wu, C.-H. Mol. Cryst. Liq. Cryst. 1996, 277, 289.
54. Illuminate, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
55. Monte Carlo multiple minimum conformational searches were carried out on a Silicon Graphics Personal Iris 4D computer for the 10-, 12-, 14-, and 16-membered-ring diametric diketones by using the MM2 force field in MACROMODEL, a molecular modeling program developed by the following: (a) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
56. (b) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
57. In the MM2-derived conformation C, the angular parameters of the γ-hydrogen (ω = 52○, Δ = 93○, θ = 113○) are very close to those found by X-ray (ω = 52○, β = 91○, θ = 113○), but the O⋯H contact distance (2.54 Å) is quite short compared to that of the solid state conformer (2.74 Å).
58. Sauers, R. Personal communication.
59. Anet, F. A. L.; St. Jacques, M.; Henrichs, P. M.; Cheng, A. K.; Krane, J.; Wong, L. Tetrahedron 1974, 30, 1629.
60. (a) Dunitz, J. D. In Perspectives in Structural Chemistry; Dunitz, J. D., Ibers, J. A., Eds.; Wiley: New York, 1968; Vol. 2, pp 1-70.
61. 15
62. (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
63. (b) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
64. (a) Zushi, S.; Kodama, Y.; Nishihata, K.; Umemura, K.; Nishio, M.; Uzawa, J.; Hirota, M. Bull Chem. Soc. Jpn. 1980, 53, 3631.
65. (b) Gough, K. M.; Millington, J. Can. J. Chem. 1995, 73, 1287.
66. (a)Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Saunders, M. J. Am. Chem. Soc. 1991, 113, 971.
67. (b) Pedireddi, V. R.; Desiraju, G. R. J. Chem. Soc., Chem Commun. 1992, 988.
68. Groth, P. Acta Chem. Scand. A 1979, 33, 203.
69. Rawdah, T. N. Tetrahedron 1991, 47, 8579.
70. Rawdah, T. N.; El-Faer, M. Z. Tetrahedron 1990, 46, 4101.
71. Furman, I.; Butcher, R. J.; Catchings, R. M.; Weiss, R. G. J. Am. Chem. Soc. 1992, 114, 6023.
72. Specific intermolecular steric interactions resulting from close contacts between molecules in the crystalline state have been shown to be capable of altering solid state photobehavior (see: Ariel, S.; Askari, S.; Evans, S.; Hwang, C.; Jay, J.; Scheffer, J. R.; Trotter, J.; Walsh, L.; Wong, Y.-F. Tetrahedron, 1987, 43, 1253), and a third possible reason for the lack of solid state photoproduct selectivity in the case of diketone 1c is that the crystal packing somehow disfavors the formation of the stereo-electronically favored cis-cyclobutanol. Inspection of the packing diagrams for this compound, however, revealed no obvious intermolecular contacts that would produce this effect.
73. Allinger, N. L.; Gorden, B.; Profeta, S., Jr. Tetrahedron 1980, 36, 859.
74. In such conformationally complex situations, the role played by conformational memory effects of the type suggested by Scaiano to be important in determining product distributions from triplet 1,4-biradicals is difficult to sort out. The situation is further complicated in the case of the macrocyclic diketones by the fact that the reactions are of mixed singlet/triplet character. Nevertheless, it is entirely possible that the solution phase photoproduct ratios for these compounds are strongly influenced by triplet biradical intersystem crossing rates, and the interested reader is referred to the following: Scaiano, J. C. Tetrahedron 1982, 38, 819.
75. Anet, F. A. L.; Cheng, A. K.; Krane, J. J. Am. Chem. Soc. 1973, 95, 7877.
76. Anet. F. A. L.; Cheng, A. K. J. Am. Chem. Soc. 1975, 97, 2420.
77. Scaiano, J. C.; Lissi, E. A.; Encina, M. V. Rev. Chem. Intermed. 1978, 2, 139.
78. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
79. 40 give a more accurate picture of the hydrogen atom abstraction geometry at the transition state.
80. TEXSAN: Crystal Structure Analysis Package (Version 5.1); Molecular Structure Corporation: The Woodlands, TX, 1985.
81. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV, pp 99-102 and 149.