Synthesis and structures of 15- and 18-membered unsaturated selenacrown ethers and their complexation with silver trifluoroacetate

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1443-1445

  Shimizu, Toshio ^a   Kawaguchi, Mari ^a   Tsuchiya, Takahiro ^a   Hirabayashi, Kazunori ^a   Kamigata, Nobumasa ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,7,10,13 PENTASELENACYCLOPENTADECA 2,5,8,11,14 PENTAENE; 1,4,7,10,13,16 HEXASELENACYCLOOCTADECA 2,5,8,11,14,17 HEXAENE; CARBON; ETHER DERIVATIVE; ETHYLENE DERIVATIVE; SELENATE; SELENIUM DERIVATIVE; SILVER DERIVATIVE; SULFUR DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; GEOMETRY; OXIDATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0141519328     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030014k     Document Type: Article

References (47)

1. (a) Macrocycle Synthesis: A Practical Approach; Parker, D., Ed.; Oxford University Press: New York, 1996; Chapter 3.
2. (b) Crown Compounds: Toward Future Applications; Cooper, S. R., Ed.; VCH Publishers: New York, 1992; Chapters 14 and 15.
3. (c) Blake, A. J.; Schröder, M. Adv. Inorg. Chem. 1990, 35, 1.
4. (d) Cooper, S. R. Acc. Chem. Res. 1988, 21, 141.
5. (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495; 7017.
6. (b) Frensdorff, H. K. J. Am. Chem. Soc. 1971, 93, 600.
7. (c) Poonia, N. S. J. Am. Chem. Soc. 1974, 96, 1012.
8. (a) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1991, 91, 1721.
9. (b) Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J. Chem. Rev. 1985, 85, 271.
10. (a) Sevdic, D.; Fekete, L.; Meider, H. J. Inorg. Nucl. Chem. 1980, 42, 885.
11. (b) Sevdic, D.; Meider, H. J. Inorg. Nucl. Chem. 1981, 43, 153.
12. Tsuchiya, T.; Shimizu, T.; Kamigata, N. J. Am. Chem. Soc. 2001, 123, 11534.
13. Tsuchiya, T.; Shimizu, T.; Hirabayashi, K.; Kamigata, N. J. Org. Chem. 2002, 67, 6632.
14. Staeb, T. H.; Gleiter, R.; Rominger, F. Eur. J. Org. Chem. 2002, 2815.
15. (a) Pinto, B. M.; Johnston, B. D.; Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D. Can. J. Chem. 1988, 66, 2956.
16. (b) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Johnston, B. D.; Pinto, B. M. J. Am. Chem. Soc. 1989, 111, 6582.
17. (c) Fujihara, H.; Yabe, M.; Ikemori, M.; Furukawa, N. J. Chem. Soc., Perkin Trans. 1 1993, 2145.
18. (a) Vogel, E.; Röhrig, P.; Sicken, M.; Knipp, B.; Herrmann, A.; Pohl, M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1651.
19. (b) Cordova-Reyes, I.; VandenHoven, E.; Mohammed, A.; Pinto, B. M. Can. J. Chem. 1995, 73, 113.
20. (c) Cordova-Reyes, I.; Hu, H.; Gu, J.-H.; VandenHoven, E.; Mohammed, A.; Holdcroft, S.; Pinto, B. M. Can. J. Chem. 1996, 74, 533.
21. (a) Kumagai, T.; Akabori, S. Chem. Lett. 1989, 1667.
22. (b) Li, W.P.; Liu, X.-F.; Xu, H.-S. Acta Chim. Sin. 1994, 52, 1082.
23. (c) Barton, A. J.; Genge, A. R. J.; Levason, W.; Reid, G. J. Chem. Soc., Dalton Trans. 2000, 2163.
24. (d) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Mehta, S.; Pinto, B. M.; Zhou, X.-M. Inorg. Chem. 2000, 39, 2558.
25. (a) Pinto, B. M.; Johnston, B. D.; Batchelor, R. J.; Gu, J.-H. J. Chem. Soc., Chem. Commun. 1988, 1087.
26. (b) Pinto, B. M.; Batchelor, R. J.; Johnston, B. D.; Einstein, F. W. B.; Gay, I. D. J. Am. Chem. Soc. 1988, 110, 2990.
27. (a) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Pinto, B. M.; Zhou, X.-M. J. Am. Chem. Soc. 1990, 112, 3706.
28. (b) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Pinto, B. M. J. Organomet. Chem. 1991, 411, 147.
29. (c) Kelly, P. F.; Levason, W.; Reid, G.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1993, 1716.
30. (d) Levason, W.; Quirk, J. J.; Reid, G.; Frampton, C. S. Inorg. Chem. 1994, 33, 6120.
31. (e) Champness, N. R.; Kelly, P. F.; Levason, W.; Reid, G.; Slawin, A. M. Z.; Williams, D. J. Inorg. Chem. 1995, 34, 651.
32. (f) Champness, N. R.; Levason, W.; Quirk, J. J.; Reid, G.; Frampton, C. S. Polyhedron 1995, 14, 2753.
33. (g) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.; Pinto, B. M.; Zhou, X. Inorg. Chem. 1996, 35, 3667.
34. (h) Levason, W.; Quirk, J. J.; Reid, G. J. Chem. Soc., Dalton Trans. 1996, 3713.
35. (i) Levason, W.; Quirk, J. J.; Reid, G.; Smith, S. M. J. Chem. Soc., Dalton Trans. 1997, 3719.
36. (j) Levason, W.; Reid, G.; Smith, S. M. Polyhedron 1997, 16, 4253.
37. (k) Davies, M. K.; Levason, W.; Reid, G. J. Chem. Soc., Dalton Trans. 1998, 2185.
38. (l) Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Pinto, B. M.; Zhou, X.-M. Can. J. Chem. 2000, 78, 598.
39. (m) Barton, A. J.; Hill, N. J.; Levason, W.; Patel, B.; Reid, G. J. Chem. Soc., Chem. Commun. 2001, 95.
40. (n) Barton, A. J.; Hill, N. J.; Levason, W.; Reid, G. J. Am. Chem. Soc. 2001, 123, 11801.
41. (o) Hill, N. J.; Levason, W.; Reid, G. Inorg. Chem. 2002, 41, 2070.
42. Hope, E. G.; Levason, W. Coord. Chem. Rev. 1993, 122, 109.
43. Bird, M. L.; Challenger, F. J. Chem. Soc. 1942, 570.
44. In this paper, unsaturated selenacrown ethers are abbreviated as x-US-y (US, unsaturated selenacrown ether; x, x-membered ring; y, number of selenium atom).
45. -3, Z = 8, orthorhombic, space group Pbca (No. 61), Rigaku AFC7R diffractometer, λ = 0.71069 Å, T = 243 K, 4018 measured reflections, 3575 unique, R1 = 0.051.
46. Atomic charges for crystal structures of 1, 2, and corresponding sulfur analogues (15-UT-5 and 18-UT-6) were calculated by using B3LYP with the LANL2DZ basis set. The calculated atomic charges (averages) are as follows. For 1: C, -0.439; H, 0.301; Se, 0.277. For 2: C, -0.450; H, 0.305; Se, 0.290. For 15-UT-5: C, -0.393; H, 0.259; S, 0.269. For 18-UT-6: C, -0.429; H, 0.301; S, 0.257.
47. -3, Z = 2, triclinic, space group P1bar (No. 2), Rigaku RAXIS-RAPID Imaging Plate, λ = 0.71069 Å, T = 173 K, 32862 measured reflections, 15700 unique, R1 = 0.086.