Relative reactivities of tethered functional groups in the interior of a zeolite

Organic Letters

Volumn 2, Issue 4, 2000, Pages 437-440

  Zhou, Wenhui ^a   Clennan, Edward L ^a  

^a UNIVERSITY OF WYOMING   (United States)

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EID: 0000440391     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991275q     Document Type: Article

References (19)

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5. (a) Thomas, J. K. Chem. Rev. 1993, 93, 301-380.
6. (b) For an elegant kinetic study, see: Cozens, F. L.; O'Neill, M.; Schepp, N. P. J. Am. Chem. Soc. 1997, 119, 7583-7584.
7. Zhou, W.; Clennan, E. L. J. Am. Chem. Soc. 1999, 121, 2915-2916.
8. 3): 2a-OOH δ 5.03 (bs, 2H), 4.49 (dd, J = 7.9, 7.8 Hz 1H), 3.0 (m, 2H), 1.7-2.0 (m, 2H), 1.68 (s, 3H); 3a-OOH δ 5.70 (dt, J = 15.7, 7.1 Hz, 1H), 5.50 (bd, J = 15.7 Hz, 1H), 3.53 (dd, J = 7.1, 1.2 Hz, 2H), 1.21 (2, 6H); 2a-OH δ 4.97 (s, 1H), 4.88 (s, 1H), 4.22 (t, J = 6.1 Hz, 1H), 3.01 (m, 2H), 1.86 (q, J = 7.0 Hz, 2H), 1.65 (s, 3H); 3a-OH δ 5.62 (d, J= 15.4 Hz, 1H), 5.69 (dt, J = 15.4, 6.5 Hz, 1H), 3.51 (d, J = 6.5 Hz, 2H), 1.20 (s, 6H); 2b-OOH δ 5.02 (bs, 1H), 4.98 (bs, 1H), 2.95 (m, 2H), 2.01 (m, 2H), 1.38 (s, 3H); 4b-OOH δ 5.26 (s, 1H), 5.08 (bs, 1H), 3.18 (t, J = 7.3 Hz, 2H), 2.52 (t, J = 7.1 Hz, 2H), 1.38 (s, 6H); 2b-OH δ 5.04 (bs, 1H), 4.90 (bs, 1H), 2.8-3.0 (m, 2H), 1.96 (m, 2H), 1.72 (bs, 3H), 1.32 (s, 3H); 4b-OH δ 5.18 (s, 1H), 4.87 (bs, 1H), 3.10 (t, J = 8.0 Hz, 2H), 2.45 (t, J = 8.0 Hz, 2H), 1.34 (s, 3H).
9. Ramamurthy, V.; Sanderson, D. R.; Eaton, D. F. J. Am. Chem. Soc. 1993, 115, 10438-10439.
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14. Clennan, E. L. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1995; Vol. IV, pp 49-80.
15. This equation was first derived by Higgins et al. (Higgins, R.; Foote, C. S.; Cheng, H. In Advances in Chemistry Series. Vol 77; American Chemical Society: Washington, DC, 1968; pp 102-117) assuming a reaction first order in singlet oxygen and substrate.
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19. This equation was derived for a reaction first order in singlet oxygen and first order in substrate. The same molecularity is most likely also observed in the zeolite and as a consequence eq 1 is adopted directly for these intrazeolite photooxidations. Nahm, K.; Foote, C. S. J. Am. Chem. Soc. 1989, 111, 1909-1910.