Site specificity in the photooxidation of some trisubstituted alkenes in thionin-supported zeolite Na-Y. On the role of the alkali metal cation

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1369-1372

  Stratakis, Manolis ^a   Froudakis, George ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001759929     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000021y     Document Type: Article

References (18)

1. Li, X.; Ramamurthy, V. Tetrahedron Lett. 1996, 37, 5235-5238.
2. Li, X.; Ramamurthy, V. J. Am. Chem. Soc. 1996, 118, 10666-10667.
3. Robins, R. J.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1997, 1071-1072.
4. Tung, C.-H.; Wang, H.; Ying Cheng, Y.-M. J. Am. Chem. Soc. 1998, 120, 5179-5184.
5. Ramamurthy, V.; Lakshminarasimhan, P. H.; Grey, C. P.; Johnston, L. J. Chem. Soc., Chem. Commun. 1998, 2411-2418.
6. Clennan, E. L.; Sram, J. P. Tetrahedron Lett. 1999, 40, 5275-5278.
7. Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657-12698.
8. For the calculation of the loading levels, see: Zhou, W.; Clennan, E. L. J. Am. Chem. Soc. 1999, 121, 2915-2916.
9. Jayathirma Rao, V.; Perlstein, D. L.; Robbins, R. J.; Lakshminarasimhan, P. H.; Kao, H.-M.; Grey, C. P.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1998, 269-270. We used limonene rearrangements as a standard (see ref 5).
10. Gaussian 94, Revision D.4; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski , V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, R.; Gomperts, R.; Martin, R. L.; Fox, D. L.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
11. Becke, D. J. Chem. Phys. 1993, 98, 5648.
12. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
13. Barich, D. H.; Xu, T.; Zhang, J.; Haw, J. F. Angew. Chem, Int. Ed. 1998, 37, 2530-2531.
14. For a review on cation-π interactions, see: Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1325.
15. Hoyau, S.; Norrman, K.; McMahon, T. B.; Ohanessian, G. J. Am. Chem. Soc. 1999, 121, 8864-8875.
16. Stratakis, M.; Orfanopoulos, M. Tetrahedron 2000, 64, 1595-1615.
17. Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1995, 36, 4291-4294.
18. Note added in proof: After this manuscript had been submitted we were informed by professor E. L. Clennan of some results similar to those reported here. We thank him for a prepublication copy of his manuscript. Clennan, E. L.; Sram, J. P. Tetrahedron, in press.