Expedient deuterolabeling of polyphenols in ionic liquids - DCl/D 2O under microwave irradiation

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5817-5819

  Hakala, Ullastiina ^a   Wähälä, Kristiina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUIDS; ISOTOPES; MICROWAVE IRRADIATION;

CARBONYL SITES; EXPEDIENT DEUTEROLABELING; POLYPHENOLIC COMPOUNDS;

PHENOLS;

BENZILIC ACID; CARBON; CARBONYL DERIVATIVE; DAIDZEIN; HYDROGEN; IONIC LIQUID; LACTONE; POLYPHENOL;

ARTICLE; CHEMICAL BINDING; ISOTOPE LABELING; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

CHLORIDES; DEUTERIUM OXIDE; FLAVONOIDS; MICROWAVES; PHENOLS;

EID: 34547137636     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070231p     Document Type: Article

References (26)

1. (a) Raffaelli, B.; Hoikkala, A.; Leppälä, E.; Wähälä, K. J. Chromatogr. B 2002, 777, 29.
2. (b) Wähälä, K.; Rasku, S.; Parikka, K. J. Chromatogr. B 2002, 777, 111.
3. Adlercreutz, H.; Kiuru, P.; Rasku, S.; Wähälä, K.; Fotsis, T. J. Steroid Biochem. Mol. Biol. 2004, 92, 399.
4. Heinonen, S.-M.; Hoikkala, A.; Wähälä, K.; Adlercreutz, H. J. Steroid Biochem. Mol. Biol. 2003, 87, 285.
5. Rasku, S; Mazur, W.; Adlercreutz, H.; Wähälä, K. J. Med. Food 1999, 2, 103.
6. Adlercreutz, H.; Fotsis, T.; Bannwart, C.; Wähälä, K.; Brunow, G.; Hase, T. Clin. Chim. Acta 1991, 199, 263.
7. Rasku, S.; Wähälä, K.; Koskimies, J.; Hase, T. Tetrahedron 1999, 55, 3445.
8. Wähälä, K.; Mäkelä, T.; Bäckström, R.; Brunow, G.; Hase, T. J. Chem. Soc., Perkin Trans. 1 1986, 95.
9. Rasku, S.; Wähälä, K. J. Labelled Compd. Radiopharm. 2000, 43, 849.
10. Soidisalo, O.; Wähälä, K. J. Labelled Compd. Radiopharm. 2006, 49, 973.
11. Ito, N.; Watahiki, T.; Maesawa, T.; Sajiki, H. Adv. Synth. Catal. 2006, 348, 1025.
12. (a) Kappe, O. C. Angew. Chem., Int. Ed. 2004, 43, 6250.
13. (b) Loupy, A. C. R. Chim. 2004, 7, 103.
14. (c) Microwave Assisted Organic Synthesis; Tierney, J. P., Lidström, P., Eds.; Blackwell Publishing: Oxford, 2005.
15. (d) Bogdal, D. Microwave-assisted Organic Synthesis: one hundred reaction procedures; Elsevier: Amsterdam, 2005.
16. (e) Kappe, C.O. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
17. (a) Jones, J. R.; Lu, S-Y. In Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: New York, 2006.
18. (b) Elander, N.; Jones, J. R.; Lu, S.-Y.; Stone-Elander, S. Chem. Soc. Rev. 2000, 29, 239.
19. (a) Hoffmann, J.; Nüchter, M.; Ondruschka, B.; Wasserscheid, P. Green Chem. 2003, 5, 296.
20. (b) Leadbeater, N. E.; Torenius, H. M.; Tye, H. Comp. Chem. High Throughput Screening 2004, 7, 511.
21. (c) Habermann, J.; Ponzi, S.; Ley, S. V. Mini-Rev. Org. Chem. 2005, 2, 125.
22. (d) Leveque, J.-M.; Cravotto, G. Chimia 2006, 60, 313.
23. Salter, R.; Bosser, I. J. Labelled Compd. Radiopharm. 2003, 46, 489.
24. Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 1915.
25. Giernoth, R.; Bankmann, D. Tetrahedron Lett. 2006, 47, 4293.
26. Rasku, S; Wähälä, K. Tetrahedron 2000, 56, 913.