Evidence for the involvement of silver nanoclusters during the wolff rearrangement of α-diazoketones

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2355-2358

  Sudrik, Surendra G ^a   Maddanimath, Trupti ^a   Chaki, Nirmalya K ^a   Chavan, Sambhaji P ^a   Chavan, Subhash P ^a   Sonawane, Harikisan R ^a   Vijayamohanan, K ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; INFRARED SPECTROSCOPY; NANOPARTICLE; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; WOLFF REARRANGEMENT; X RAY ANALYSIS;

EID: 0141518497     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034747g     Document Type: Article

References (24)

1. Doyle, M. P.; Mckervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazocompounds; Wiley: New York, 1998.
2. Gill, G. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; John Wiley: New York, 1991; Vol. 3, pp 887-909.
3. Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091.
4. Meier, H.; Zeller, K. P. Angew. Chem., Int. Ed. Engl. 1975, 14, 32.
5. Bachmann, W. E.; Struve, W. S. Org. React. 1946, 1, 38.
6. Zhu, Z.; Bally, T.; Stracener, L. L.; Mcmahon, R. J. J. Am. Chem. Soc. 1997, 121, 2863.
7. Likhotvorik, I.; Zhu, Z.; Tae, E. L.; Tippmann, E.; Hill, B. T.; Platz, M. S. J. Am. Chem. Soc. 2001, 123, 6061.
8. Scott, A. P.; Platz, M. S.; Radom, L. J. Am. Chem. Soc. 2001, 123, 6069.
9. Mueller, A.; Vogt, C.; Sewald, N. Synthesis 1998, 837.
10. Lindler, M. R.; Podlech, J. Org. Lett. 2002, 3, 1849.
11. Sudrik, S. G.; Chavan, S. P.; Chandrakumar, K. R. S.; Pal, S.; Date, S. K.; Chavan, S. P.; Sonawane, H. R. J. Org. Chem. 2002, 67, 1574.
12. Yuhawa, Y.; Tsuno, Y.; Ibata, T. Bull. Chem. Soc. Jpn. 1967, 40, 2613.
13. Yuhawa, Y.; Tsuno, Y.; Ibata, T. Bull. Chem. Soc. Jpn. 1967, 40, 2618.
14. Furniss, B. S.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; ELBS-Longmann: London, 1978; p 485.
15. Newman, M. S.; Beal, P. F. J. Am. Chem. Soc. 1950, 72, 3.
16. Lee, V.; Newman, M. S. Org. Synth. 1970, 50, 77.
17. Aiken, J. D., III; Aiken, R. G. J. Mol. Catal. A.: Chem. 1999, 145, 1.
18. Henglein, A. J. Phys. Chem. 1993, 97, 457.
19. Mulvaney, P. In Semiconductors Nanoclusters-Physical, Chemical, and Catalytic Aspects; Kamat, P. V., Meisel, D., Eds.; Elsevier: Amsterdam, 1987, pp 99-124.
20. Brust, M.; Walker, M.; Bethell, D.; Schiffrin, D. J.; Whyman, R. J. Chem. Soc., Chem. Commun. 1994, 801. We prepared silver nanoclusters using silver(I) benzoate and sodium borohydride as the reducing agent. Deliberate addition of this nanocluster to α-diazoketone 1 gives Wolff rearranged carboxylic acid 3 in 80% chemical yield.
21. Cohen, S. G.; Parola, A.; Parsons, G. Chem. Rev. 1973, 73, 141.
22. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, Fundamentals and Applications; Wiley: New York, 2001.
23. Parker, K. A.; Su, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: England, 1995; Vol. 6, pp 4465-4467.
24. Edelstein, A. S.; Cammaratal, R. C. Nanaomaterials Synthesis, Properties and Applications; Bristol, 1996; p 10.