Stereoselective photodimerization of (E)-stilbenes in crystalline γ- cyclodextrin inclusion complexes

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8098-8104

  Rao, K S S P ^a   Hubig, S M ^a   Moorthy, J N ^a   Kochi, J K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA CYCLODEXTRIN; STILBENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; DIMERIZATION; PHOTOCHEMISTRY; STEREOCHEMISTRY;

EID: 0033615581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9903149     Document Type: Article

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39. Note that 1,2,3,4,5-pentafluorostilbene, which crystallizes in tightly packed π-stacks with an intermolecular distance of about 3.5 A, is the only stilbene derivative that photodimerizes in the crystalline state (in a head-to-tail configuration). See: Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkowsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641.
40. (a) Bouwstra, J. A.; Schouten, A.; Kroon, J. Acta Crystallogr., Sect. C 1984, 40, 428. (b) Hoekstra, H. A.; Meertens, P.; Vos, A. Acta Crystallogr. 1975, B31, 2813. Bernstein, J. Acta Crystallogr. 1975, B31, 1268. Finder, C. J.; Newton, M. G.; Allinger, N. L. Acta Crystallogr. 1974, B31, 411. (e) Robertson, J. M.; Woodward, I. Proc. R. Soc. London, Ser. A 1937, 162, 568.
41. (a) Bouwstra, J. A.; Schouten, A.; Kroon, J. Acta Crystallogr., Sect. C 1984, 40, 428. (b) Hoekstra, H. A.; Meertens, P.; Vos, A. Acta Crystallogr. 1975, B31, 2813. Bernstein, J. Acta Crystallogr. 1975, B31, 1268. Finder, C. J.; Newton, M. G.; Allinger, N. L. Acta Crystallogr. 1974, B31, 411. (e) Robertson, J. M.; Woodward, I. Proc. R. Soc. London, Ser. A 1937, 162, 568.
42. (a) Bouwstra, J. A.; Schouten, A.; Kroon, J. Acta Crystallogr., Sect. C 1984, 40, 428. (b) Hoekstra, H. A.; Meertens, P.; Vos, A. Acta Crystallogr. 1975, B31, 2813. Bernstein, J. Acta Crystallogr. 1975, B31, 1268. Finder, C. J.; Newton, M. G.; Allinger, N. L. Acta Crystallogr. 1974, B31, 411. (e) Robertson, J. M.; Woodward, I. Proc. R. Soc. London, Ser. A 1937, 162, 568.
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46. 32
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48. 28,33c,d On the other hand, if preorientation B is photoactive (it may not undergo photocycloaddition due to insufficient π-orbital overlap between the crossed double bonds), it will result in the formation of the anti-cyclobutane. Thus, the fact that syn-cyclobutanes are obtained stereoselectively in good yields suggests that the stilbene guests in the γ-CD channels preferentially stack with parallel orientation (A). (b) Ding, J.; Steiner, T.; Saenger, W. Acta Crystallogr. Sect. B 1991, 47, 731. Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1992, 33, 1013. Inokuma, S.; Yamamoto, T.; Nishimura, J. Tetrahedron Lett. 1990, 31, 97.
49. 28,33c,d On the other hand, if preorientation B is photoactive (it may not undergo photocycloaddition due to insufficient π-orbital overlap between the crossed double bonds), it will result in the formation of the anti-cyclobutane. Thus, the fact that syn-cyclobutanes are obtained stereoselectively in good yields suggests that the stilbene guests in the γ-CD channels preferentially stack with parallel orientation (A). (b) Ding, J.; Steiner, T.; Saenger, W. Acta Crystallogr. Sect. B 1991, 47, 731. Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1992, 33, 1013. Inokuma, S.; Yamamoto, T.; Nishimura, J. Tetrahedron Lett. 1990, 31, 97.
50. 28,33c,d On the other hand, if preorientation B is photoactive (it may not undergo photocycloaddition due to insufficient π-orbital overlap between the crossed double bonds), it will result in the formation of the anti-cyclobutane. Thus, the fact that syn-cyclobutanes are obtained stereoselectively in good yields suggests that the stilbene guests in the γ-CD channels preferentially stack with parallel orientation (A). (b) Ding, J.; Steiner, T.; Saenger, W. Acta Crystallogr. Sect. B 1991, 47, 731. Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1992, 33, 1013. Inokuma, S.; Yamamoto, T.; Nishimura, J. Tetrahedron Lett. 1990, 31, 97.
51. 28,33c,d On the other hand, if preorientation B is photoactive (it may not undergo photocycloaddition due to insufficient π-orbital overlap between the crossed double bonds), it will result in the formation of the anti-cyclobutane. Thus, the fact that syn-cyclobutanes are obtained stereoselectively in good yields suggests that the stilbene guests in the γ-CD channels preferentially stack with parallel orientation (A). (b) Ding, J.; Steiner, T.; Saenger, W. Acta Crystallogr. Sect. B 1991, 47, 731. Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1992, 33, 1013. Inokuma, S.; Yamamoto, T.; Nishimura, J. Tetrahedron Lett. 1990, 31, 97.
52. Owing to the channel-type arrangement of γ-CD inclusion complexes in the crystalline state (see Figure 1), we avoid the misleading picture of separated 1:1 and 2:1 complexes of stilbene with cyclodextrin in the crystal lattice and prefer the simple distinction between stilbene guests with and without a close neighbor.
53. The possibility of more than two distinct locations for the stilbene cannot be excluded since the kinetic traces can also be fitted with more than two exponentials.
54. 15
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