A new reaction of bisphenol A and preparation of polysubstituted 9,9-dimethylxanthenes

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1058-1063

  Caruso, Andrew J ^a   Lee, Julia L ^a  

^a GE GLOBAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030987953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961766d     Document Type: Article

References (47)

1. 1b (a) Ourisson, G.; Chazan, J. B. Bull. Soc. Chim. Fr. 1968, 1374. (b) Ibid. 1968, 1384.
2. 1b (a) Ourisson, G.; Chazan, J. B. Bull. Soc. Chim. Fr. 1968, 1374. (b) Ibid. 1968, 1384.
3. Xanthene dianhydrides related to 9 show promise as components of nearly rodlike polyimides. Trofimenko, S. US Patent 5,051,520, Sept 24, 1991. Auman, B. C.; Trofimenko, S. Macromolecules 1994, 27, 1136.
4. Xanthene dianhydrides related to 9 show promise as components of nearly rodlike polyimides. Trofimenko, S. US Patent 5,051,520, Sept 24, 1991. Auman, B. C.; Trofimenko, S. Macromolecules 1994, 27, 1136.
5. Xanthene-4,5-dicarboxylates bearing pendant alkyl groups form the structural basis of synthetic replicators, molecular compliments to imides and molecular clefts. Nowick, J. S.; Ballester, P.; Ebmeyer, F.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 8902. Park, T. K.; Schroeder, J.; Rebek, J., Jr. Ibid. 1991, 113, 5125. Park, T. K.; Feng, Q.; Rebek, J., Jr. Ibid. 1992, 114, 4529.
6. Xanthene-4,5-dicarboxylates bearing pendant alkyl groups form the structural basis of synthetic replicators, molecular compliments to imides and molecular clefts. Nowick, J. S.; Ballester, P.; Ebmeyer, F.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 8902. Park, T. K.; Schroeder, J.; Rebek, J., Jr. Ibid. 1991, 113, 5125. Park, T. K.; Feng, Q.; Rebek, J., Jr. Ibid. 1992, 114, 4529.
7. Xanthene-4,5-dicarboxylates bearing pendant alkyl groups form the structural basis of synthetic replicators, molecular compliments to imides and molecular clefts. Nowick, J. S.; Ballester, P.; Ebmeyer, F.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 8902. Park, T. K.; Schroeder, J.; Rebek, J., Jr. Ibid. 1991, 113, 5125. Park, T. K.; Feng, Q.; Rebek, J., Jr. Ibid. 1992, 114, 4529.
8. Caruso, A. J.; Lee, J. L. US Patent 5,466,777, Nov 14, 1995; 5,504,184, Apr 2, 1996.
9. Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R.J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. J. Org. Chem. 1958, 23, 544. Inoue, K. US Patent 4,594,459, Jun 10, 1986. Nagayo, T.; Otsubo, T.; Kuno, S.; limuro, S. JP 62,148,441, Jul 2, 1987; Chem. Abstr. 1988, 109, 149054x. Crivello, J. V.; Ramdas, A. J. J. Mater. Sci. Pure Appl. Chem. 1992, A29(9), 753.
10. Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R.J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. J. Org. Chem. 1958, 23, 544. Inoue, K. US Patent 4,594,459, Jun 10, 1986. Nagayo, T.; Otsubo, T.; Kuno, S.; limuro, S. JP 62,148,441, Jul 2, 1987; Chem. Abstr. 1988, 109, 149054x. Crivello, J. V.; Ramdas, A. J. J. Mater. Sci. Pure Appl. Chem. 1992, A29(9), 753.
11. Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R.J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. J. Org. Chem. 1958, 23, 544. Inoue, K. US Patent 4,594,459, Jun 10, 1986. Nagayo, T.; Otsubo, T.; Kuno, S.; limuro, S. JP 62,148,441, Jul 2, 1987; Chem. Abstr. 1988, 109, 149054x. Crivello, J. V.; Ramdas, A. J. J. Mater. Sci. Pure Appl. Chem. 1992, A29(9), 753.
12. Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R.J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. J. Org. Chem. 1958, 23, 544. Inoue, K. US Patent 4,594,459, Jun 10, 1986. Nagayo, T.; Otsubo, T.; Kuno, S.; limuro, S. JP 62,148,441, Jul 2, 1987; Chem. Abstr. 1988, 109, 149054x. Crivello, J. V.; Ramdas, A. J. J. Mater. Sci. Pure Appl. Chem. 1992, A29(9), 753.
13. Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R.J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. J. Org. Chem. 1958, 23, 544. Inoue, K. US Patent 4,594,459, Jun 10, 1986. Nagayo, T.; Otsubo, T.; Kuno, S.; limuro, S. JP 62,148,441, Jul 2, 1987; Chem. Abstr. 1988, 109, 149054x. Crivello, J. V.; Ramdas, A. J. J. Mater. Sci. Pure Appl. Chem. 1992, A29(9), 753.
14. Tashiro, M.; Watanabe, H.; Oe, K. Org. Prep. Proced. Int. 1975, 7, 189.
15. Olah, G. A.; Kaspi, J.; Meidar, D. Synthesis 1978, 396.
16. Morgan, T. A. US Patent 4,806,673, Feb 21, 1989.
17. Krimm, H.; Ruppert, H.; Schnell, H. US Patent 3,418,371, Dec 24, 1968. Hefner, R. E., Jr. US Patent 4,683,276, Jul 28, 1987.
18. Krimm, H.; Ruppert, H.; Schnell, H. US Patent 3,418,371, Dec 24, 1968. Hefner, R. E., Jr. US Patent 4,683,276, Jul 28, 1987.
19. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
20. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
21. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
22. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
23. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
24. (a) o-Cresol, 2,6-dimethylphenol, p-cresol, 2,3,6-trimethylphenol, and 2,6-dichlorophenol: Mark, V.; Hedges, C. V. US Patent 4,560808, Dec 24, 1985. (b) Catechol: Tomioka, A.; Nakanishi, H.; Kuwana, K.; Kamiya, Y.; Hanabatake, M.; Oi, S. JP 02,172,936, Dec 26, 1988; Chem. Abstr, 1990, 113, 221391g. 2,6-Diphenylphenol: Wang, Z. Y.; Hay, A. S. Synthesis 1989, 471. Resorcinol: Ito, M.; Iimuro, S. JP 04,364,147, Oct 8, 1990; Chem. Abstr. 1993, 118, 233643g.
25. Farnham, A. G. US Patent 3,288,864, Nov 29, 1966.
26. Curtis, R. F. J. Chem. Soc. 1962, 415. Krimm, H.; Buysch, H. J. Ger. Offen. 2,645,020, Apr 13, 1978; Chem. Abstr. 1978, 89, 24036e. Faler, G. R.; Lynch, J. C. US Patent 4,701,566, Oct 20, 1987.
27. Curtis, R. F. J. Chem. Soc. 1962, 415. Krimm, H.; Buysch, H. J. Ger. Offen. 2,645,020, Apr 13, 1978; Chem. Abstr. 1978, 89, 24036e. Faler, G. R.; Lynch, J. C. US Patent 4,701,566, Oct 20, 1987.
28. Curtis, R. F. J. Chem. Soc. 1962, 415. Krimm, H.; Buysch, H. J. Ger. Offen. 2,645,020, Apr 13, 1978; Chem. Abstr. 1978, 89, 24036e. Faler, G. R.; Lynch, J. C. US Patent 4,701,566, Oct 20, 1987.
29. Curtis, R. F. J. Chem. Soc. 1962, 415. Krimm, H.; Buysch, H. J. Ger. Offen. 2,645,020, Apr 13, 1978; Chem. Abstr. 1978, 89, 24036e. Faler, G. R.; Lynch, J. C. US Patent 4,701,566, Oct 20, 1987.
30. Neumann, F. W.; Smith, W. E. J. Org. Chem. 1966, 31, 4318.
31. Spirobiindan 17 was found to be stable under the reaction conditions.
32. Baker, W.; Besly, D. M. J. Chem. Soc. 1940, 1103.
33. Baker, W.; Besly, D. M. J. Chem. Soc. 1939, 195. Baker, W.; McOmie, J. F. W.; Wild, J. H. Ibid. 1957, 3060.
34. Baker, W.; Besly, D. M. J. Chem. Soc. 1939, 195. Baker, W.; McOmie, J. F. W.; Wild, J. H. Ibid. 1957, 3060.
35. Divakar, K. J.; Rao, A. S. Synth. Commun. 1976, 6, 423.
36. Reilly, J; Drumm, P. J.; Barrett, H. S. B. J. Chem. Soc. 1927, 67.
37. Pfeifer, J.; Duthaler, R. US Patent 4,714,669, Dec 22, 1987.
38. Wust, A.; Hammerstroem, K. US Patent 4,325,789, Apr 20, 1982.
39. Carnahan, J. C. US Patent 4,277,628, Jul 7, 1981.
40. Caruso, A. J.; Lee, J. L. US Patent 5,430,199, Jul 4, 1995.
41. Zaugg, H. E.; Michaels, R. J. J. Org. Chem. 1974, 39, 351. Mesiters, A.; Mole, T. Aust. J. Chem. 1974, 27, 1655.
42. Zaugg, H. E.; Michaels, R. J. J. Org. Chem. 1974, 39, 351. Mesiters, A.; Mole, T. Aust. J. Chem. 1974, 27, 1655.
43. Ebner, J.; Reily, D. In Active Oxygen in Chemistry; Foote, C. S., Silverstone-Valentine, J., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: Glasgow, 1995. Oxidations of this type are conveniently carried out as described in: Wheeler, T. N.; Craig, T. A.; Morland, R. B.; Ray, J. A. Synthesis 1987, 883.
44. Ebner, J.; Reily, D. In Active Oxygen in Chemistry; Foote, C. S., Silverstone-Valentine, J., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: Glasgow, 1995. Oxidations of this type are conveniently carried out as described in: Wheeler, T. N.; Craig, T. A.; Morland, R. B.; Ray, J. A. Synthesis 1987, 883.
45. Friedman, L. Org. Synth. 1963, 43, 80.
46. Caruso, A. J.; Lee, J. L. manuscript in preparation.
47. g's for the corresponding polyesters based on ethylene glycol and dimethyl terephthalate (PET) and ethylene glycol and dimethyl naphthalene-2,6-dioate (PEN) are 81 and 125 °C, respectively. Yoon, K. H.; Lee, S. C.; Park, O. O. Polymer J. 1994, 26, 816.