Formation of a novel sulfonated enedione

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2556-2558

  Lockshin, Mary P ^a   Filosa, Michael P ^a   Zuraw, Michael J ^a   Carlier, Paul R ^b  

^a POLAROID CORPORATION   (United States)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5244363686     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9520856     Document Type: Article

References (22)

1. (a) Rodd's Chemistry of Carbon Compounds; Coffey, S., Ed.; Elsevier. Amsterdam, 1974; Vol. 3, pt. B, pp 36-116.
2. (b) The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley Interscience: New York, 1974; Part 2, pp 880-949.
3. Redox equilibria may sometimes complicate the reaction, giving the reduced starting quinone, the substituted quinone, and products of multiple substitution/oxidation. Youngblood, M. J. Org. Chem. 1986, 51, 1981.
4. (a) Ogata, Y.; Sawaki, Y.; Isono, M. Tetrahedron 1969, 25, 2715.
5. (b) Ogata, Y.; Sawaki, Y.; Isono, M. Tetrahedron 1970, 26, 731.
6. (a) Takahashi, O.; Furutacho, N.; Morigaki, M., Fuji Photo Film Co., Ltd. Eur. Patent Appl. EP 305926, Mar. 8, 1989.
7. (b) Morigaki, M.; Ishikawa, T.; Andoh, K.; Seto, N.; Ueda, S.; Koshimizu, T., Fuji Photo Film Co., Ltd. Eur. Patent Appl. EP 294769, Dec 14, 1988.
8. In photographic systems sulfinate anion performs the same function as sulfite which has long been used as a preservative of developer solutions and a stain preventative. Sulfite both retards aerial oxidation and adds nucleophilically to quinones to form colorless hydroquinone mono- and disulfonates rather than highly colored products. For a brief discussion of the use of sulfite in developing solutions, see the following reference: The Theory of the Photographic Process, 4th ed.; James, T. H., Ed.; Macmillan: New York, London, 1977; pp 309-310
9. Brown, E. R.; Finley, K. T.; Reeves, R. L. J. Org. Chem. 1971, 36, 2849.
10. NaOCl is a convenient oxidant for hydroquinones: Ishii, F.; Kishi, K. Synthesis 1980, 9, 706-8.
11. 2.6 03. 10 05.9]-undecane-8,-11-dione is well known: (a) Cookson, R. C.; Crundwell, E.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3062. (b) Marchand, A.; Allen, R. J. Org. Chem. 1974, 39, 1596. (c) Galin, F. Z.; Afonichev, D. D.; Lerman, B. M.; Kazakov, V. P.; Tolstikov, G. A. Zh. Org. Khim. 1978, 14, 2308.
12. 2.6 03. 10 05.9]-undecane-8,-11-dione is well known: (a) Cookson, R. C.; Crundwell, E.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3062. (b) Marchand, A.; Allen, R. J. Org. Chem. 1974, 39, 1596. (c) Galin, F. Z.; Afonichev, D. D.; Lerman, B. M.; Kazakov, V. P.; Tolstikov, G. A. Zh. Org. Khim. 1978, 14, 2308.
13. 2.6 03. 10 05.9]-undecane-8,-11-dione is well known: (a) Cookson, R. C.; Crundwell, E.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3062. (b) Marchand, A.; Allen, R. J. Org. Chem. 1974, 39, 1596. (c) Galin, F. Z.; Afonichev, D. D.; Lerman, B. M.; Kazakov, V. P.; Tolstikov, G. A. Zh. Org. Khim. 1978, 14, 2308.
14. The carbon numbering system of 5 in Scheme 2 is designed to facilitate the following discussion; the standard IUPAC numbering for 5 and related derivatives is used in the Experimental Section.
15. Wiberg, K. B.; Bonneville, G.; Dempsey, R. Isr. J. Chem. 1983, 23, 85.
16. Rogers, D. W.; Choi, L. S.; Girellini, R. S.; Holmes, T. J.; Allinger, N. L. J. Phys. Chem. 1980, 84, 1810.
17. Nucleophilic attack at the phenyl-substituted quinone carbon (C-2) does not reduce the ring strain of the ring-fused norbornadiene system and would thus remain reversible.
18. AM1 geometry optimization calculations were carried out on a Silicon Graphics Personal Iris 4D/35 using Spartan 1.0.
19. Lau, P. T. S.; Kestner. M. J. Org. Chem. 1962, 33, 4426.
20. Reported 2,6:2,5 ratios of the hydroquinone addition products: for quinone 10, 93:7; for quinone 11, 90:10.
21. Kice, J.; Bowers, K. J. Am. Chem Soc. 1962, 7, 605.
22. Porter, R F.; Rees, W. W.; Frauenglass, E; Willius, H. S., III; Nawn, G. H.; Chiesa, P. P.; Gates, J. W., Jr. J. Org. Chem. 1964, 29, 588.