Spirodienone and Bis(spirodienone) Derivatives of Calix[4]naphthalenes

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1819-1826

  Georghiou, Paris E ^a   Ashram, Muhammad ^a   Clase, Howard J ^a   Bridson, John N ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000708439     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971541i     Document Type: Article

References (21)

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2. Litwak, A. M.; Grynszpan, F.; Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Org. Chem. 1993, 58, 393.
3. Aleksiuk, O.; Grynszpan, F.; Litwak, A. M.; Biali, S. E. New J. Chem. 1996, 20, 473.
4. Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun., 1993, 11.
5. Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645.
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7. Van Gelder, J. M.; Brenn, J.; Thondorf, I.; Biali, S. E. J. Org. Chem. 1997, 62, 3511.
8. Abel, J. Ber. 1892, 25, 3477.
9. Shearing, E. A.; Smiles, S. J. Chem. Soc. 1937, 1931.
10. Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron 1993, 49, 135.
11. Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron 1993, 49, 135.
12. Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron 1993, 49, 135.
13. There is an erroneous reference to 7 and 8, referred to as structures 2 and 3 in ref 2, which was subsequently corrected: J. Org. Chem. 1993, 58, 5024.
14. Georghiou, P. E.; Ashram, M.; Li, Z.-P.; Chaulk, S. G. J. Org. Chem. 1995, 60, 7284.
15. Grynszpan, F.; Alexsiuk, O.; Biali, S. E. J. Org. Chem. 1994, 59, 2070.
16. Andreetti, G. D.; Bohmer, V.; Jordon, G.; Tabatabai, M.; Ugozzoli, F.; Vogt, W.; Wolff, A. J. Org. Chem. 1993, 58, 4023.
17. Li, Z. Synthesis and properties of calix[4]naphthalenes. Ph.D. Dissertation, Memorial University of Newfoundland, St. John's, New-foundland, Canada, Jan 1996.
18. In this paper, "axial" protons, indicated by the subscript "a", refer to bridging methylene group protons that are directed above, or below, the annulus; "equatorial" protons, indicated by the subscript "e", refer to bridging methylene group protons that are pointing away from and are out of the plane of the annulus; the methylene protons on the tetrahydrofuran rings are designated "α" or "β" to designate those that are located, respectively, below, or above the plane of the annulus, as depicted in formulas 13, 14, 20, and 21.
19. Georghiou, P. E.; Ashram, M. J. Org. Chem. 1995, 60, 2909.
20. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
21. Atomic coordinates for all structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.