Pure and Applied Chemistry

Pure Appl. Chem., 2007, Vol. 79, No. 6, pp. 993-1001

http://dx.doi.org/10.1351/pac200779060993

New mechanisms centered on reactive intermediates: Examples from diazirine and carbene chemistry

References

• 1. R. A. Moss. Acc. Chem. Res. 39, 267 (2005). (http://dx.doi.org/10.1021/ar050155h)
• 2. W. H. Graham. J. Am. Chem. Soc. 87, 4396 (1965). (http://dx.doi.org/10.1021/ja00947a040)
• 3. (a). K. B. Eisenthal, R. A. Moss, N. J. Turro. Science 225, 1439 (1984); (http://dx.doi.org/10.1126/science.225.4669.1439)
• 3. (b). R. A. Moss, N. J. Turro. In Kinetics and Spectroscopy of Carbenes and Nitrenes, M. S. Platz (Ed.), pp. 213-238, Plenum Press, New York (1990);
• 3. (c). R. A. Moss, M. S. Platz, M. Jones Jr. (Eds.). Reactive Intermediate Chemistry, John Wiley, New York (2004).
• 4. (a). J. Wlostowska, R. A. Moss, W. Guo, M. J. Chang. Chem. Commun. 432 (1982);
• 4. (b). D. P. Cox, R. A. Moss, J. Terpinski. J. Am. Chem. Soc. 105, 6513 (1983). (http://dx.doi.org/10.1021/ja00359a038)
• 5. (a). W. P. Dailey. Tetrahedron Lett. 28, 5801 (1987); (http://dx.doi.org/10.1016/S0040-4039(01)81057-1)
• 5. (b). X. Creary, A. F. Sky. J. Org. Chem. 53, 4637 (1988); (http://dx.doi.org/10.1021/jo00254a057)
• 5. (c). K. E. Bainbridge, W. P. Dailey. Tetrahedron Lett. 30, 4901 (1989); (http://dx.doi.org/10.1016/S0040-4039(01)80537-2)
• 5. (d). X. Creary, A. F. Sky. J. Am. Chem. Soc. 112, 368 (1990). (http://dx.doi.org/10.1021/ja00157a056)
• 6. (a). T. Martinu, W. P. Dailey. J. Org. Chem. 71, 5012 (2006); (http://dx.doi.org/10.1021/jo060341g)
• 6. (b). X. Creary. Acc. Chem. Res. 25, 31 (1992). (http://dx.doi.org/10.1021/ar00013a005)
• 7. (a). R. A. Moss. Acc. Chem. Res. 13, 58 (1980); (http://dx.doi.org/10.1021/ar50146a005)
• 7. (b). R. A. Moss. Acc. Chem. Res. 22, 15 (1989); (http://dx.doi.org/10.1021/ar00157a003)
• 7. (c). R. A. Moss. In Carbene Chemistry from Fleeting Intermediates to Powerful Reagents, G.Bertrand (Ed.), pp. 57-101, Dekker-Fontis, New York (2002).
• 8. R. A. Moss. Acc. Chem. Res. 32, 969 (1999). (http://dx.doi.org/10.1021/ar9900212)
• 9. J. E. Jackson, M. S. Platz. In Advances in Carbene Chemistry, Vol. 1, U. H. Brinker (Ed.), pp. 89-160, JAI Press, Greenwich, CT (1994).
• 10. J. E. Jackson, N. Soundararajan, M. S. Platz, M. T. H. Liu. J. Am. Chem. Soc. 110, 5595 (1988). (http://dx.doi.org/10.1021/ja00224a068)
• 11. R. Bonneau, M. T. H. Liu, M. T. Rayez. J. Am. Chem. Soc. 111, 5973 (1989). (http://dx.doi.org/10.1021/ja00197a086)
• 12. E. J. Dix, M. S. Herman, J. L. Goodman. J. Am. Chem. Soc. 115, 10424 (1993). (http://dx.doi.org/10.1021/ja00075a094)
• 13. M. T. H. Liu, R. Bonneau. J. Am. Chem. Soc. 111, 6873 (1989). (http://dx.doi.org/10.1021/ja00199a075)
• 14. R. A. Moss, J. Tian, R. R. Sauers, K. Krogh-Jespersen. Submitted for publication.
• 15. R. Bonneau, M. T. H. Liu. J. Phys. Chem. A 104, 4115 (2000). (http://dx.doi.org/10.1021/jp993711w)
• 16. K. Krogh-Jespersen, S. Yan, R. A. Moss. J. Am. Chem. Soc. 121, 6269 (1999). (http://dx.doi.org/10.1021/ja990148m)
• 17. E. M. Tippmann, M. S. Platz, I. B. Svir, O. V. Klymenko. J. Am. Chem. Soc. 126, 5750 (2004). (http://dx.doi.org/10.1021/ja039693k)
• 18. M. T. H. Liu, R. Bonneau, J. Am. Chem. Soc. 112, 3915 (1990). (http://dx.doi.org/10.1021/ja00166a028)
• 19. G.-J. Ho, K. Krogh-Jespersen, R. A. Moss, S. Shen, R. S. Sheridan, R. Subramanian. J. Am. Chem. Soc. 111, 6875 (1989). (http://dx.doi.org/10.1021/ja00199a077)
• 20. G. Yao, P. Rempala, C. Bashmore, R. S. Sheridan. Tetrahedron Lett. 40, 17 (1999). (http://dx.doi.org/10.1016/S0040-4039(98)80006-3)
• 21. J.-M. Fede, S. Jockush, N. Lin, R. A. Moss, N. J. Turro. Org. Lett. 5, 5027 (2003). (http://dx.doi.org/10.1021/ol030123z)
• 22. R. A. Moss, G. Chu, R. R. Sauers. J. Am. Chem. Soc. 127, 2408 (2005). (http://dx.doi.org/10.1021/ja050103n)
• 23. D. M. Lemal, Y. Wei. Org. Lett. 6, 3837 (2004) report CO at 2117 and 2171 cm-1.
• 24. A. A. Korkin, P. v. R. Schleyer, R. J. Boyd. Chem. Phys. Lett. 227, 312 (1994).
• 25. J. A. Berson, D. M. Birney, W. P. Dailey, J. F. Liebman. In Modern Models of Bonding and Delocalization, J. F. Liebman, A. Greenberg (Eds.), pp. 391-441, VCH, Weinheim (1988).
• 26. P. Horsewood, G. W. J. Kirby. J. Chem. Soc., Perkin Trans. 1 1587 (1980). (http://dx.doi.org/10.1039/p19800001587)
• 27. (a). M. Regitz. (Ed.). Carbene, Carbenoide, Methoden der Organische Chemie (Houben-Weyl), Vol. E19b, Thieme Verlag, Stuttgart (1989);
• 27. (b). J. Hine. Divalent Carbon, Ronald Press, New York (1964);
• 27. (c). M. Fedorynski. Chem. Rev. 103, 1099 (2003). (http://dx.doi.org/10.1021/cr0100087)
• 28. M. Jones Jr., W. H. Sachs, A. Kulczycki Jr., F. J. Waller. J. Am. Chem. Soc. 88, 3167 (1966). (http://dx.doi.org/10.1021/ja00965a072)
• 29. J. F. Hartwig, M. Jones Jr., R. A. Moss, W. Lawrynowicz. Tetrahedron Lett. 27, 5907 (1986). (http://dx.doi.org/10.1016/S0040-4039(00)85359-9)
• 30. S. I. Presblski, A. Zorba, D. M. Thamattor, E. M. Tippmann, M. S. Platz. Tetrahedron Lett. 45, 485 (2004). (http://dx.doi.org/10.1016/j.tetlet.2003.11.009)
• 31. J. E. Chateauneuf, R. P. Johnson, M. M. Kirchoff. J. Am. Chem. Soc. 112, 3217 (1990). (http://dx.doi.org/10.1021/ja00164a056)
• 32. D. E. Milligan, M. E. Jacox. J. Chem. Phys. 47, 703 (1967). (http://dx.doi.org/10.1063/1.1711942)
• 33. G. L. Closs, J. J. Coyle. J. Am. Chem. Soc. 87, 4270 (1965). (http://dx.doi.org/10.1021/ja00947a010)
• 34. G. Chu, R. A. Moss, R. R. Sauers. J. Am. Chem. Soc. 127, 14206 (2005). (http://dx.doi.org/10.1021/ja055656c)
• 35. R. A. Moss, J. Tian, R. R. Sauers, D. H. Ess, K. N. Houk, K. Krogh-Jespersen. J. Am. Chem. Soc. In press.