Synthesis of 2-Aryl-10b,10c-dimethyl-10b,10c-dihydropyrenes and a Study of Their Conjugation Behavior: Linear Relationship between the Degree of Conjugation and the Electronic Nature of Substituents

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4412-4417

  Lai, Yee Hing ^a   Jiang, Jianping ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001650538     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962337i     Document Type: Article

References (58)

1. (a) Mills, W. H. Chem. Ind. (London) 1926, 45, 884, 905.
2. (b) Stoughton, R. W.; Adams, R. J. Am. Chem. Soc. 1932, 54, 4426.
3. (c) Stanley, W. M.; Adams, R. J. Am. Chem. Soc. 1930, 52, 1200.
4. (d) Beaven, G. H.; Hall, D. M.; Lesslie, M. S.; Turner, E. E.; Bird, G. R. J. Chem. Soc. 1954, 131.
5. (e) Braude, E. A.; Forbes, W. F. J. Chem. Soc. 1955, 3776.
6. (f) Murrell, J. N. J. Chem. Soc. 1956, 3779.
7. (a) Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 42, 2339.
8. (b) Campbell, N.; Barclay, B. M. Chem. Rev. 1947, 40, 359.
9. (c) Dermer, O. C.; Edmison, M. T. Chem. Rev. 1957, 57, 77.
10. (a) Ullmann, F. Chem. Ber. 1903, 36, 2382.
11. (b) Bunnell, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 392.
12. (c) Schulenberg, J. W.; Archer, S. Org. React. 1965, 14, 19.
13. (d) Yamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86.
14. (e) Renger, B. Synthesis 1985, 856.
15. (a) Hayashi, T.; Hayashizaki, K.; Kiyo, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
16. (b) Saa, J. M.; Martorell, G. J. Org. Chem. 1993, 58, 1963.
17. (c) Anderson, J. C.; Namli, H. Synlett 1995, 765.
18. (d) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776 and references cited therein.
19. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
20. Watanable, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
21. Lai, Y.-H.; Chen, P.; Peck, T.-G. Pure Appl. Chem. 1993, 65, 81.
22. Kende, A. S.; Liebeskind, L. S.; Braitsch, D. Tetrahedron Lett. 1975, 3375.
23. (a) Mitchell, E. H.; Mahadevan, R. Tetrahedron Lett. 1981, 22, 5131.
24. (b) Mitchell, R. H.; Iyer, V. S.; Khalifa, N.; Mahadevan, R.; Venugopalan, S.; Weerawarna, S. A.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 1514.
25. Phillips, J. B.; Molyneux, R. J.; Sturm, E.; Boekeiheide, V. J. Am. Chem. Soc. 1967, 89, 1704.
26. (a) Rosenberg, D. E.; Beadle, J. R. Tetrahedron Lett. 1980, 21, 4141.
27. (b) Beadle, J. R.; Korzeniowski, H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594.
28. (a) Abramovitch, R. A.; Gadallah, F. F. J. Chem. Soc. B 1968, 497.
29. (b) Kobayashi, M.; Minato, H.; Yamada, E.; Kobori, N. Bull. Chem. Soc. Jpn. 1970, 43, 215.
30. (c) Kaul, B. L.; Zollinger, H. Helv. Chim. Acta 1968, 51, 2132.
31. Burri, P.; Zollinger, H. Helv. Chim. Acta 1973, 56, 232.
32. Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, 5116.
33. Mitchell, R. H.; Chen, Y. Tetrahedron Lett. 1996, 37, 5239.
34. Wallis, J. D.; Easton, R. J. C.; Dunitz, J. D. Helv. Chim. Acta 1993, 76, 1411.
35. (a) Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228.
36. (b) Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH Publishers: Deerfieid Beach, FL, 1985.
37. Clar, E. Polycyclic Hydrocarbons; Academic Press-Springer Verlag: London, 1964; Vol. 2.
38. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
39. (b) Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1980, 4, 1.
40. (a) Exner, O. Correlation Analysis of Chemical Data; Plenum Press: New York, 1988.
41. (b) Shorter, J. Correlation Analysis of Organic Reactivity; Wiley: Chichester, 1982.
42. (c) Shorter, J. In Correlation Analysis in Chemistry: Recent Advances; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978.
43. (d) Exner, O. In Advances in Linear Free Energy Relationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1972.
44. (e) Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970.
45. (a) Shorter, J. Aust. J. Chem. 1995, 48, 1453.
46. (b) Reis, J. C.; Segurado, M. A. P.; De Oliveira, J. D. G. J. Phys. Org. Chem. 1995, 8, 5.
47. (c) Shorter, J. Pure Appl. Chem. 1994, 66, 2451.
48. (d) Charton, M. Prog. Phys. Org. Chem. 1987, 16, 287.
49. (e) Wells, R. P.; Ehrenson, S.; Taft, R. W. Prog. Phys. Org. Chem. 1968, 6, 147.
50. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979.
51. (a) Swain, C. G.; Lupton, E. C. J. Am. Chem. Soc. 1968, 90, 4328.
52. (b) Wells, P. R. Linear Free Energy Relationships; Academic Press: New York, 1968.
53. Based on the MM2(87) force field with expanded parameter sets; See: Bays, J. P. J. Chem. Educ. 1992, 62, 209.
54. Serena Software, P.O. Box 3076, Bloomington, IN 47402-3076.
55. (a) Fukazawa, Y.; Ogata, K.; Usui, S. J. Am. Chem. Soc. 1988, 110, 8692.
56. (b) Longuet-Higgins, H. C.; Salem, L. Proc. R. Soc. (London) 1960, A257, 445.
57. (c) Mallion, R. B. Mol. Phys. 1973, 25, 1415.
58. Stewart, J. J. P. MOPAC v6.0, Program 455, QCPE, University of Indiana: Bloomington, IN.