A phenyliodonium ylide as a precursor for dicarboethoxycarbene: Demonstration of a strategy for carbene generation [1]

Journal of the American Chemical Society

Volumn 122, Issue 21, 2000, Pages 5210-5211

  Camacho, Margaret B ^a   Clark, Aurora E ^a   Liebrecht, Tabitha A ^a   DeLuca, JoAnn P ^a  

^a CENTRAL WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DIPHENYLIODONIUM SALT;

CALCULATION; DECOMPOSITION; HEAT; LETTER; PHOTOCHEMISTRY; PHOTOLYSIS; PRECURSOR; REACTION ANALYSIS; SYNTHESIS;

EID: 0034738043     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000334o     Document Type: Letter

References (24)

1. (a) Frey, H. M.; Stevens, I. D. R. J. Chem. Soc. 1965, 3101.
2. (b) Mansoor, A. M.; Stevens, I. D. R. Tetrahedron Lett. 1966, 1733.
3. Chang, K.-T.; Shechter, H. J. Am. Chem. Soc. 1979, 101, 5082.
4. Chambers, G. R.; Jones, M., Jr. J. Am. Chem. Soc. 1980, 102, 4516.
5. (e) Modarelli, D. A.; Morgan, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 7034.
6. Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971.
7. (a) Jones, M., Jr.; Ando, W.; Hendrick; M. E.; Kulczycki, A.; Howley, P. M.; Hummel, K. F.; Malament, D. S. J. Am. Chem. Soc. 1972, 94, 7469.
8. (b) Wulfman, D. S.; Poling, B.; McDaniel, R. S., Jr. Tetrahedron Lett. 1975, 4519.
9. Wang, J.-L.; Toscano, J. P.; Platz, M. S.; Nicolaev, V.; Popik, V. J. Am. Chem. Soc. 1995, 117, 5477.
10. See, for example: (a) Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981.
11. (b) Fox, M. J.; Scacheri, J. E. G.; Jones, K. G.; Jones, M., Jr.; Shevlin, P. B.; Armstrong, B.; Sztyrbicka, R. Tetrahedron Lett. 1992, 33, 5021.
12. Armstrong, B. M.; McKee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685.
13. Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, R.; Abbot, S. C.; Kirchhoff, M. M. J. Am. Chem. Soc. 1998, 120, 8055.
14. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
15. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
16. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
17. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y ; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 (Revision E.2); Gaussian, Inc.: Pittsburgh, PA, 1995.
19. 2, -48 (calcd) vs -52 (exptl).
20. (b) Experimental heats of formation from Mallard, W. G., Ed. NIST Chemistry WebBook; http:// www.nist.gov/chemistry/.
21. (a) Neiland, O.; Karele, B. J. Org. Chem. USSR (Engl. Transl.) 1965, 1, 1854.
22. (b) Schank, K.; Lick, C. Synthesis 1983, 392.
23. max = 280 nm in benzene solution.
24. Barltrop, J. A.; Coyle, J. D. Excited States in Organic Chemistry; John Wiley & Sons: New York, 1975.