Sodium amalgam: A highly efficient reagent for the detosylation of azathiacrown ethers

Synthesis

Volumn , Issue 5, 2006, Pages 756-758

  Forshee, Philip B ^a   Sibert, John W ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

Author keywords

Crown compounds; Ligands; Macrocycles; Reductions; Supramolecular chemistry

Indexed keywords

ETHERS; HAZARDOUS MATERIALS;

CROWN COMPOUNDS; LIGANDS; MACROCYCLES;

SODIUM;

10 (4 TOLYLSULFONYL) 1,4,7 TRITHIA 10 AZACYCLODODECANE; 10,13 BIS (4 TOLYLSULFONYL) 1,4,7 TRITHIA 10 13 DIAZACYCLOPENTADECANE; 10,13,16 TRIS(4 TOLYLSULFONYL) 1,4,7 TRITHIA 10,13,16 TRIAZACYCLOOCTADECANE; 11 (4 TOLYLSULFONYL) 1,4,7 TRITHIA 11 AZACYCLOTETRADECANE; AMALGAM; IONOPHORE; MACROCYCLIC COMPOUND; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DEPROTECTION REACTION; DETOSYLATION;

EID: 33644912294     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926338     Document Type: Article

References (19)

1. Comprehensive Supramolecular Chemistry, Vol. 1; Gokel, G. W.; Atwood, J. L.; Davies, J. E.; MacNicol, D. D.; Vögtle, F., Eds.; Pergamon: Oxford, 1996.
2. (a) Cooper, S. R.; Rawle, S. C. Struct. Bonding (Berlin) 1990, 72, 1.
3. (b) Blake, A. J.; Schröder, M. Adv. Inorg. Chem. 1990, 35, 1.
4. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Aza-Crown Macrocycles, In Chemistry of Heterocyclic Compounds, Vol. 51; Taylor, E. C., Ed.; Wiley: New York, 1993.
5. For example, see: Glenny, M. A.; Blake, A. J.; Wilson, C.; Schröder, M. J. Chem. Soc., Dalton Trans. 2003, 194; and references cited therein.
6. Tanaka, M.; Nakamura, M.; Ikeda, T.; Ikeda, K.; Ando, H.; Shibutani, Y.; Yajima, S.; Kimura, K. J. Org. Chem. 2001, 66, 7008.
7. Hart, S. M.; Boeyens, J. A. C.; Michael, J. P.; Hancock, R. D. J. Chem. Soc., Dalton Trans. 1983, 1601.
8. Chak, B.; McAuley, A.; Whitcombe, T. W. Inorg. Chim. Acta 1996, 246, 349.
9. Blake, A. J.; Lippolis, V.; Schröder, M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2004, 60, o901.
10. McAuley, A.; Subramanian, S. Inorg. Chem. 1990, 29, 2830.
11. Sibert, J. W.; Forshee, P. B.; Lynch, V. Inorg. Chem. 2005, 44, 8602.
12. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 39, 3477.
13. Vriesema, B. K.; Butler, J.; Kellogg, R. M. J. Org. Chem. 1984, 49, 110.
14. Sessler, J. L.; Sibert, J. W.; Hugdahl, J. D.; Lynch, V. Inorg. Chem. 1989, 28, 1417.
15. In our procedure, the reaction was performed without external heat under an argon atmosphere with the reaction apparatus placed in an oil bath. After initiating the reaction by addition of a small amount of mercury to the sodium metal, the remaining mercury was immediately and quickly added (approx. 10-15 s total addition time) via an addition funnel with rapid stirring at room temperature. The amounts of reagents and reaction workup were as reported in ref. 15.
16. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; Wiley: New York, 1967, 1030.
17. van de Water, L. A.; Buijs, W.; Driessen, W. L.; Reedijk, J. New J. Chem. 2001, 25, 243.
18. Westerby, B. C.; Juntunen, K. L.; Leggett, G. H.; Pett, V. B.; Koenigbauer, M. J.; Purgett, M. D.; Taschner, M. J.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1991, 30, 2109.
19. Atkins, T. J.; Richman, J. E.; Oettle, W. F. Org. Synth. 1978, 58, 86.