Sulfur-bridged molecular racks: O,S-sesquinorbornadienes, CNS-[3] andCNOS-[4]polynorbornanes

Arkivoc

Volumn 2002, Issue 6, 2002, Pages 234-256

  Margetic, Davor ^a   Butler, Douglas N ^a   Warrener, Ronald N ^a  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

Author keywords

7 thianorbornenes; AM1; Cycloaddition; High pressure; Modelling

Indexed keywords

12,14 DIOXA 15 THIAPENTACYCLO[4.4.3.1 2,5 .1 7,10 .0 1,6 ]PENTADECA 3,8 DIENE 11,13 DIONE; 16,19 DIOXA 18 THIAHEXACYCLO[8.4.3.1 2,9 .1 11,14 .0 1,10 .0 3,8 ]NONADECA 3,5,7,12 TETRAENE 15,17 DIONE; 7 OXANORBORNADIENE 2,3 DICARBOXYLIC ANHYDRIDE; 7 THIANORBORNENE; ACID ANHYDRIDE; BRIDGED COMPOUND; CARBOXYLIC ACID DERIVATIVE; DIMETHYL 22 BENZYL 17 METHYL 17,22 DIAZA 24 THIAHEPTACYCLO[10.9.1.1 3.10 .0 2,11 .0 4,9 .0 13,21 .0 15,19 ]TRICOS 4,6,8 TRIENE 1,12 DICARBOXYLATE; DIMETHYL 31 BENZYL 26,29 DIOXO 31 AZA 28,30 DIOXA 33 THIAUNDECACYCLO[16.8.3.1 2.17 .1 4,15 .1 6,13 .1 19,26 .0 1,18 .0 3,16 .0 5,14 .0 7,12 .0 20,25 ]TRITRIACONT 7,9,11,20,22,24 HEXAENE 4,15 DICARBOXYLATE; FURAN; ISOBENZOTHIOPHENE; MALEIC ANHYDRIDE; MALEIMIDE DERIVATIVE; N METHYLMALEIMIDE; N PHENYLMALEIMIDE; NAPHTHALENE 2,3 DICARBOXYLIC ANHYDRIDE; NORBORNANE DERIVATIVE; PHTHALIC ANHYDRIDE; SULFUR; THIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; FRAGMENTATION REACTION; HIGH TEMPERATURE; MOLECULAR MODEL; PRESSURE; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY; SYNTHESIS;

EID: 3242767726     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Johnston, M. R.; Gunter, M. J.; Warrener, R. N. Tetrahedron, 2002, 58, 3445-3451.
2. Johnston, M. R.; Gunter, M. J.; Warrener, R. N. Chem. Commun. 1998, 2739-2740.
3. (a) Flamigni, L.; Talarico, A. M.; Barigelletti, F.; Johnston, M. R. Photochem. Photobiol. Sci. 2002, 1, 190-197;
4. (b) Flamigni, L.; Johnston, M. R. New J. Chem. 2001, 25, 1368-1370.
5. (a) Johnston, M. R.; Latter, M. J.; Warrener, R. N. Aust. J. Chem. 2001, 54, 633-636;
6. (b) Johnston, M. R.; Latter, M.J.; Warrener, R. N. Chem. Commun. 2002, in press.
7. Foley, P. J.; Butler, D. N.; Russell, R. A.; Warrener, R. N., unpublished results;
8. (b) Foley, P. J. PhD Thesis, Central Queensland University, 2002.
9. Warrener, R. N. Eur. J. Org. Chem. 2000, 20, 3363-3380.
10. (a) Warrener, R. N. Chem. Aust., 1992, 59, 578-581;
11. (b) Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Amer. Chem. Soc., 1994, 116, 3645-3646.
12. Warrener, R. N.; Margetic, D.; Sun, G.; Amarasekara, A. S.; Foley, P.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1999, 40, 4111-4114.
13. A German patent recorded the preparation of CO-, OS- and SS-sesquinorbornenes under reaction conditions that are neither reproducible in our hands nor are the proposed reactions plausible in the light of current knowledge in the field. Unless the experimental details are incomplete, then this report must be discounted.
14. Jung, J. C.; Roh, C. H.; Jung, M. H.; Kong, K. K.; Lee, G. S.; Baik, K. H. Ger. Offen. 2000, 70 pp. CA 132:214771.
15. Kotsuki, H.; Kitagawa, S.; Nishizava, H.; Tokoroyama, T. J. Org. Chem. 1978, 43, 1471-1472; Kotsuki, H.; Nishizava, H.; Kitagawa, S.; Ochi, M.; Yamasaki, N.; Matsuoka, K.; Tokoroyama, T. Bull Chem. Soc. Jpn. 1979, 52, 544-548.
16. Kotsuki, H.; Kitagawa, S.; Nishizava, H.; Tokoroyama, T. J. Org. Chem. 1978, 43, 1471-1472; Kotsuki, H.; Nishizava, H.; Kitagawa, S.; Ochi, M.; Yamasaki, N.; Matsuoka, K.; Tokoroyama, T. Bull Chem. Soc. Jpn. 1979, 52, 544-548.
17. Drew, M. G. B.; George, A. V.; Isaacs, N. S.; Rzepa, H. S., J. Chem. Soc., Perkin Trans 1, 1985, 1277-1284.
18. Butler, D. N.; Margetic, D.; O'Neill, P. J. C.; Warrener, R. N. Synlett 2000, 98-100.
19. Li, Y.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M. J. Org. Chem. 1997, 62, 7926-7936.
20. Isobenzothiophene was generated by dehydrogenation of 2-thiaindane with DDQ using the method of Hart and Sasaoka. It was stable in solution overnight and used in situ for cycloaddition reactions conducted in dichloromethane or chloroform.
21. Cava, M. P.; Deana, A. A. J. Amer. Chem. Soc. 1959, 89, 4266-4288, Bandgar, B. P.; Savavarte, V. S.; Pawar, S. G.; Kamble, V. T., Ind. J. Hetero. Chem., 2000, 10, 159-160.
22. Cava, M. P.; Deana, A. A. J. Amer. Chem. Soc. 1959, 89, 4266-4288, Bandgar, B. P.; Savavarte, V. S.; Pawar, S. G.; Kamble, V. T., Ind. J. Hetero. Chem., 2000, 10, 159-160.
23. Hart, H.; Sasaoka, M. J. Amer. Chem. Soc. 1978, 100, 4326-4327.
24. For an early PMO treatment of site selectivity in dimethyl 7-oxanorbornadiene-2,3-dicarboxylate and related norbornadienes, see Warrener, R. N.; Anderson, C. M.; McCay, I. W.; Paddon-Row, M. N., Aust. J. Chem., 1977, 30, 1481-1507.
25. The introduction of oxygen or substituted nitrogen at the 7-position of norbornenes considerably increased the dienophilicity (and dipolarophilicity) of the olefinic -bond both to electron-deficient and regular-demand Diels-Alder dienes. Metal-catalysed [2+2] addition of acetylenes were also promoted.
26. (a) s-Tetrazines: Warrener, R. N. J. Amer. Chem. Soc., 1971, 93, 2346-2348;
27. (b) 1,3,4-Oxadiazoles: Warrener, R. N.; Margetic, D.; Tiekink, E. R. T.; Russell, R. N. Synlett, 1997, 196-198;
28. (c) Cyclopentadiene: Warrener, R. N.; Wang, S.; Russell, R. A. Tetrahedron, 1997, 53, 3975-3990;
29. (d) Cyclobutene epoxides (thermal): Warrener, R. N.; Schulz, A. C.; Butler, D. N.; Wang, S.; Mahadevan, I. B.; Russell, R. A., Chem. Commun. 1997, 1023-1024;
30. (e) Cyclobutene epoxides (photochemical): Margetic, D.; Russell, R. A.; Warrener, R. N., Org. Lett., 2000, 2, 4003-4006.
31. (a) Mitsudo T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanake, Y. Takegami, Y., J. Org. Chem., 1979, 44, 4492-4496;
32. Chao, K. C.; Rayabarapu, D. K.; Wang, C.-C.; Cheng, C.-H., J. Org. Chem., 2001, 66, 8804-8810.
33. (a) Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N., Synlett, 1998, 588-589;
34. (b) Butler, D. N.; Hammond, M. L. A.; Johnston, M. R.; Sun, G.; Malpass, J. R.; Fawcett, J.; Warrener, R. N., Org. Lett., 2000, 2, 721-724.
35. Warrener, R. N. Prog. Heterocyclic. Chem. 2001, 13, 25-51.
36. (a) Del Mazza, D.; Reinecke, M. Heterocycles 1980, 14, 647-649;
37. (b) Del Mazza, D.; Reinecke, M. J. Org. Chem., 1988, 53, 5799-5806.
38. (a) Haddadin, M. J.; Chelhot, N. C.; Pieridou, M. J. Org. Chem. 1974, 39, 3278-3281;
39. (b) Roland, M. M.; Anderson, R. C. J. Heterocycl. Chem. 1977, 14, 541-543.
40. Effenberger, F.; Ziegler, T., Chem. Ber. 1987, 120, 1339-1346.
41. Warrener, R. N.; Elsey, G. M.; Maksimovic, L.; Johnston, M. R. Tetrahedron Lett., 1995, 36, 7753-7756.
42. (a) Mantzaris, J.; Weissberger, E. J. Org. Chem., 1974, 39, 726-728;
43. (b) Margetic, D.; Johnston, M. R.; Warrener, R. N.; Butler, D. N. ECSOC-5 (contribution a0037), http://www.molpi.net/ecsoc-5 (Sept 2001).