Synthesis of selectively deuterated fulvenes and indenes from enediynes

Organic and Biomolecular Chemistry

Volumn 3, Issue 2, 2005, Pages 218-221

  Peabody, Scott W ^a   Breiner, Boris ^a   Kovalenko, Serguei V ^a   Patil, Satish ^a   Alabugin, Igor V ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL BONDS; DEUTERIUM; DNA; HYDROGEN; PROTONS; SOLVENTS; SYNTHESIS (CHEMICAL);

HYDROGEN ATOMS; HYDROGENOLYSIS; ISOTOPOMERS;

AROMATIC COMPOUNDS;

EID: 12844255829     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417493n     Document Type: Article

References (31)

1. (a) H. Alt and A. Köppl, Chem. Rev., 2000, 100, 1205;
2. (b) S. Lin and R. Waymouth, Acc. Chem. Res., 2002, 35, 765.
3. K. Kondo, H. Goda, K. Takemoto, H. Aso, T. Sasaki, K. Kawakami, H. Yoshida and K. Yoshida, J. Mat. Chem., 1992, 2, 1097.
4. (a) J. Vicente, J. Abad and J. Gil-Rubio, Organometallics, 1995, 14, 2677;
5. (b) A. Korte, J. Legros and C. Bolm, Synlett, 2004, 13, 2397.
6. S. Galton and R. Abbas, J. Org. Chem., 1973, 38, 2008.
7. M. Suarez, R. Duguid and H. Morrison, J. Am. Chem. Soc., 1989, 111, 6384.
8. V. Ranade and R. Prins, Chem. Eur. J., 2000, 6, 313.
9. J. O'Connor, S. Friese and M. Tichenor, J. Am. Chem. Soc., 2002, 124, 3506.
10. (a) Cycloalkene-cycloalkene transformations via platina(IV) cyclobutane derivatives: B. Williams and P. Jennings, Inorg. Chim. Acta, 1997, 265, 23;
11. (b) sigmatropic rearrangements: A. Padwa, S. Goldstein, R. Loza and M. Pulwer, J. Org. Chem., 1981, 46, 1858;
12. (c) dioxygenase-catalysed hydroxylation: D. Boyd, N. Sharma, N. Bowers, R. Boyle, J. Harrison, K. Lee, T. Bugg and D. Gibson, Org. Biomol. Chem., 2003, 1, 1298;
13. (d) rearrangements: E. Friedrich and D. Taggart, J. Org. Chem., 1975, 40, 720;
14. (e) addition of thiols: H. Szmant and J. Baeza, J. Org. Chem., 1980, 45, 4902.
15. (a) I. V. Alabugin and S. V. Kovalenko, J. Am. Chem. Soc., 2002, 124, 9052;
16. (b) theoretical study: I. V. Alabugin and M. Manoharan, J. Am. Chem. Soc., 2003, 125, 4495.
17. H. W. Whitlock, P. E. Sandvick, L. E. Overman and P. B. Reichard, J. Org. Chem., 1969, 34, 879.
18. S. V. Kovalenko, S. Peabody, M. Manoharan, R. S. Clark and I. V. Alabugin, Org. Lett., 2004, 6, 2457.
19. B. König, W. Pitsch, M. Klein, R. Vasold, M. Prall and P. Schreiner, J. Org. Chem., 2001, 66, 1742.
20. J. Johnson, D. Bringley, E. Wilson, K. Lewis, L. Beck and A. Matzger, J. Am. Chem. Soc., 2003, 125, 14708.
21. J. Scott, S. Parkin and J. Anthony, Synlett, 2004, 1, 161.
22. 1H NMR and high-resolution MS are in perfect agreement with each other. See Supplementary Information† for details.
23. T. J. Burkey, M. Majewski and D. Griller, Adv. Free Radical Chem. (Greenwich, Conn.), 1990, 1, 159.
24. D. D. M. Wagner and D. Griller, J. Am. Chem. Soc., 1986, 108, 2218.
25. (a) For the interconnection of reaction and activation energies in hydrogen transfer reactions, see: J. P. Roth, J. C. Yoder, T.-J. Won and J. M. Mayer, Science, 2002, 294, 2524;
26. (b) I. V. Alabugin, M. Manoharan, B. Breiner and F. Lewis, J. Am. Chem. Soc., 2003, 125, 9329;
27. (c) for the seminal theoretical treatment, see: R. A. Marcus, J. Phys. Chem., 1968, 72, 891.
28. From a practical point of view, it is important to work up the reaction mixtures expediently since prolonged exposure to base leads to facile hydrogen exchange at the endocydic methylene group. This exchange is especially fast in bis-TFP indenes where it can be used for selective D-labeling at this position.
29. (a) J. Leblanc and C. Moise, J. Organomet. Chem., 1976, 120, 65;
30. (b) G. Knox and P. Pauson, J. Chem. Soc., 1961, 4615.
31. L. Friedman and F. M. Logullo, J. Org. Chem., 1969, 34, 3089.