Structure and photochemistry of 18-diazo-1,4,7,10,13,16- hexaoxacyclononadeca-17,19-dione and its sodium and potassium complexes. Control of the ground-state conformation of 2-diazo-1,3-dicarbonyl fragment via host-guest complexation

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 9867-9873

  Bogdanova, Aneta ^a   Perkovic, Marc W ^b   Popik, Vladimir V ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

^b WESTERN MICHIGAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; METHANOL; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS; POTASSIUM; X RAY CRYSTALLOGRAPHY;

CARBONYL GROUPS; SODIUM IONS; X-RAY CRYSTAL STRUCTURE;

COMPLEXATION;

18 DIAZO 1,4,7,10,13,16 HEXAOXACYCLONONADECA 17,19 DIONE; 2 DIAZO 1,3 DICARBONYL; 2,4 DIOXO 19 CROWN 6; 3 METHOXY 2,4 DIOXO 19 CROWN 6; ALPHA,ALPHA' DICARBONYLCARBENE; CARBENE; CARBENOID; CARBONYL DERIVATIVE; CROWN ETHER DERIVATIVE; DIAZOMALONATE DERIVATIVE; METHANOL; POTASSIUM ION; SODIUM DERIVATIVE; SODIUM ION; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; GEOMETRY; PHOTOCHEMICAL EFFICIENCY; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; POTASSIUM; SODIUM; STEREOISOMERISM; ULTRAVIOLET RAYS;

EID: 28044442084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051594x     Document Type: Article

References (68)

1. (a) Kirmse, W. Eur. J. Org. Chem. 2002, 2193.
2. (b) Meier, H.; Zeller, K.-P. Angew. Chem., Int. Ed. Engl. 1975, 14, 32.
3. (c) Zeller, K.-P.; Meier, H.; Muller, E. Tetrahedron 1972, 28, 5831.
4. (a) Regitz, M.; Maas, G. Diazo compounds: properties and synthesis; Academic Press: Orlando, FL, 1986.
5. (b) The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; J. Wiley: New York, 1978.
6. Tidwell, T. T. Ketenes; J. Wiley: New York, 1976; pp 84-100.
7. Moreau, W. M. Semiconductor Lithography; Plenum Press: New York, 1988.
8. Reiser, A. Photoreactive Polymers: The Science and Technology of Resists; Wiley: New York, 1989.
9. Reichmanis, E.; Thompson, L. F. Chem. Rev. 1989, 89, 1273.
10. Arndt-Eistert homologation of carboxylic acids: (a) Maas, G. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; Thieme Verlag: Stuttgart, 1989; Vol. 19b/2, 1022.
11. (b) Ye, T.; McKervey, A. M. Chem. Rev. 1994, 94, 1091.
12. (c) Jones, M.; Moss, R. A. Carbenes; Wiley: New York, 1973.
13. (d) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Intersciences: New York, 1998; pp 487-534.
14. Ring contraction: refs 2a, 5d and (e) Fessner, W.-D.; Prinzbach, H.; Rihs, G. Tetrahedron Lett. 1983, 24, 5857.
15. (f) Ghosh, A.; Banerjee, U. K.; Venkateswaran, R. V. Tetrahedron 1990, 46, 3077.
16. (g) Lawton, G.; Moody, C. J.; Pearson, C. J. J. Chem. Soc., Perkin Trans. 1 1987, 877.
17. (h) Moody, C. J.; Pearson, C. J.; Lawton, G. Tetrahedron Lett. 1985, 26, 3167.
18. Redmore, D.; Gutsche, C. D. Adv. Alicyclic. Chem. 1971, 3, 125.
19. Preparation of β-keto acid derivatives: Cossy, J.; Belotti, D.; Thellend, A.; Pete, J. P. Synthesis 1988, 720.
20. Korobitsyna, I. K.; Nikolaev, V. A. Zh. Org. Khim. 1976, 12, 1251.
21. Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219.
22. Photoaffinity labeling: Davioud, E.; Fagat, J.; Souque, A.; Rafestin-Oblin, M.-E.; Marquet, A. J. Med. Chem. 1996, 39, 2860.
23. Somack, R.; Nordeen, S. K.; Eberhardt, N. L. Biochemistry 1982, 21, 5651.
24. Photonuclease: Nakatani, K.; Maekawa, S.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1996, 118, 10635.
25. Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007.
26. Wender, P. A.; Touami, S. M.; Alayrac, C.; Philipp, U. C. J. Am. Chem. Soc. 1996, 118, 6522.
27. (a) Toscano, J. P. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 216-245.
28. (b) Jones, M.; Moss, R. A. Carbenes; Wiley: New York, 1973.
29. (c) Zollinger, H. Diazo chemistry: 2. Aliphatic, inorganic, and organometallic compounds; VCH Publishers: New York, 1995; pp 305-357.
30. (d) Kirmse, W. Carbenes and the O-H bond in: Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press, Inc.: Greenwich, CT, 1994; pp 1-57.
31. (e) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 40, 10811.
32. α-Diazocarbonyl compounds: Kaplan, F.; Meloy, G. K. Tetrahedron Lett. 1964, 2427.
33. Kaplan, F.; Meloy, G. K. J. Am. Chem. Soc. 1966, 88, 950.
34. Kessler, H.; Rosenthal, D. Tetrahedron Lett. 1973, 393.
35. Curci, R.; DiFuria, F.; Lucchini, V. Spectrosc. Lett. 1974, 7, 211.
36. Lichter, R. L.; Srinivasan, P. R.; Smith, A. B., III; Dieter, R. K; Denny, C. T. Chem. Commun. 1977, 366.
37. Dickert, F. L.; Soliman, F. M.; Bestmann, H. J. Tetrahedron Lett. 1982, 23, 2639.
38. Diazo-1,3-diketones: Nikolaev, V. A.; Rodina, L. L.; Korobitsyna, I. K. Zh. Org. Khim. 1974, 10, 1555.
39. Lauer, W.; Krause, V.; Wengenroth, H.; Meier, H. Chem. Ber. 1988, 121, 465.
40. Nikolaev, V. A.; Popik, V. V. Zh. Org. Khim. 1989, 25, 1014.
41. Kaplan, F.; Mitchell, M. L. Tetrahedron Lett. 1979, 9, 759.
42. Zeller, K.-P. Chem. Ber. 1979, 112, 678.
43. Fenwick, J.; Prater, G.; Ogi, K.; Strausz, O. P. J. Am. Chem. Soc. 1973, 95, 124.
44. Torres, M.; Ribo, J.; Clement, A.; Strausz, O. P. Can. J. Chem. 1983, 61, 996.
45. Bogdanova, A.; Popik, V. V. J. Am. Chem. Soc. 2004, 126, 11293.
46. Bogdanova, A.; Popik, V. V. J. Am. Chem. Soc. 2003, 125, 14153.
47. Christensen, J. J.; Eatough, D. J.; Izatt, R. M. Chem. Rev. 1974, 74, 351;
48. Bradshaw, J. S. In Synthetic Multidentate Macrocyclic Compounds; Izatt, R. M., Christensen, J. J., Eds.; Academic Press: New York, 1978; pp 53-109.
49. Izatt, R. M.; Nelson, D. P.; Rytting, J. H.; Haymore, B. L.; Christensen, J. J. J. Am. Chem. Soc. 1971, 93, 1619.
50. Dalley, N. K. In Synthetic Multidentate Macrocyclic Compounds; Izatt, R. M., Christensen, J. J., Eds.; Academic Press: New York, 1978; pp 207-243.
51. Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. In Comprehensive Supramolecular Chemistry; Davies, J. E. D., Ripmeester, J. A., Eds.; Pergamon Press: Oxford, 1996; Vol. 8, pp 425-482.
52. Cox, B.; Schneider, H. In Coordination and Transport Properties of Macrocyclic Compounds in Solution; Elsevier Publishing Co., Inc.: New York, 1992; pp 58-62.
53. Huheey, J. E.; Keiter, E. A.; Keiter R. L. In Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed.; HarperCollins: New York, 1993.
54. Izatt, R. M.; Lamb, J. D.; Maas, G. E.; Asay, R. E.; Bradshaw, J. S.; Christensen, J. J. J. Am. Chem. Soc. 1977, 99, 2365.
55. Liu, Y.; Zhang, L.; Li, Y.; Chen, Y.; S., H.; J., M.; Inoue, Y.; Ouchi, M. Thermochim. Acta 1995, 253, 93.
56. Supporting Information; see the paragraph at the end of this paper regarding availability.
57. Nikolaev, V. A.; Popik, V. V.; Korobitsyna, I. K. Zh. Org. Khim. 1991, 27, 505.
58. (a) Wang, J.-L.; Toscano, J. P.; Platz, M. S.; Nikolaev, V.; Popik, V. J. Am. Chem. Soc. 1995, 117, 5477.
59. (b) Jones, M., Jr.; Ando, W.; Hendrick, M. E.; Kulczucki, A.; Howley, P. M.; Hummel, K. F.; Malament, D. S. J. Am. Chem. Soc. 1972, 94, 7469.
60. (Chem. Soc. Chim. Fr. 1973, 2065.
61. Hadel, L. M.; Maloney, V. M.; Platz, M. S.; McGimpsey, W. G.; Scaiano, J. C. J. Phys. Chem. 1986, 90, 2488.
62. (a) Livinghouse, T.; Stevens, R. V. J. Am. Chem. Soc. 1978, 100, 6479.
63. (b) Nikolaev, V. A.; Khimich, N. N.; Korobitsyna, I. K. Khim. Geterotsikl. Soedin. 1985, 321.
64. (c) Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551.
65. (d) Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702.
66. (e) Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708.
67. (f) Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
68. Popik, V. V The Role of Molecular Geometry in the Wolff Rearrangement of α-Diazocarbonyl Compounds: Conformational Control or Structural Constraints? Can. J. Chem. 2005, 83 (9), in press, CHEM-05-021-PI.