Biphotonic generation of carbenes and carbocations by laser flash photolysis

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1197-1200

  Kirmse, Wolfgang ^a   Krzossa, Birgit ^a   Steenken, Steen ^b  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; LASER; PHOTOLYSIS; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0030062789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02416-6     Document Type: Article

References (24)

1. (a) For a review, see: Kirmse, W. in Advances in Carbene Chemistry, Brinker, U. H., Ed.; Jai Press: Greenwich, Conn., 1994; Vol 1, pp. 1-57.
2. (b) Kirmse, W.; Meinert, T.; Modarelli, D. A.; Platz, M. S. J. Am. Chem. Soc. 1993, 115, 8918.
3. (c) Kirmse, W.; Meinert, T. J. Chem. Soc., Chem. Commun. 1994, 1065.
4. (d) Kirmse, W.; Strehlke, I. K.; Steenken, S. J. Am. Chem. Soc. 1995, 117,
5. Kirmse, W.; Kilian, J.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 6399.
6. Chateauneuf, J. E. J. Chem. Soc., Chem. Commun. 1991, 1437.
7. Belt, S. T.; Bohne, C.; Charette, G.; Sugamori, S. E.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 2200.
8. For the reactivity of diazo compounds toward Brønsted acids, see: Regitz, M.; Maas, G. Diazo Compounds, Academic Press: Orlando, Fla., 1986; Chapter 3, and references cited therein.
9. (a) Felix, D.; Müller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 1276.
10. (b) Felix, D.; Wintner, C.; Eschenmoser, A. Org. Synth. 1988, Coll. Vol. 6, 679.
11. (a) Maier, G.; Gebhardt, J., results reported in Angew. Chem. 1988, 100, 317; Angew. Chem., Int. Ed. Engl. 1988, 27, 309.
12. (a) Maier, G.; Gebhardt, J., results reported in Angew. Chem. 1988, 100, 317; Angew. Chem., Int. Ed. Engl. 1988, 27, 309.
13. (b) Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981.
14. 3): δ 4.0 (br.s, 2 H), 7.0-7.7 (m, 17 H), 8.30 (dd, J = 8/2 Hz, 1 H).
15. (b) Müller, R. K.; Joos, R.; Felix, D.; Schreiber, J.; Wintner, C.; Eschenmoser, A. Org. Synth. 1988, Coll. Vol. 6, 56.
16. McClelland, R. A.; Kanagasabapathy, V. M.; Steenken, S. J. Am. Chem. Soc. 1988, 110, 6913
17. Deno, N. C.; Evans, W. L. J. Am. Chem. Soc. 1957, 79, 5804.
18. McClelland, R. A.; Banait, N.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 2829.
19. McClelland, R. A.; Mathivanan, N.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 4857.
20. The half life of 3c was obtained by extrapolating conventional rate measurements in HFIP-acetonitrile mixtures (56-83% HFIP) to neat HFIP.
21. 2
22. The cation 6c can be generated by LFP of 5c in HFIP. However, excitation of 5c in the present experiments is unlikely, owing to an excess of the strongly absorbing 1c. Addition of an equimolar amount of 5c prior to LFP of 1c did not significantly enhance the yield (OD) of 6c. Thus, the sequence 4c → 5c → 6c is excluded as an alternative route to 6c.
23. max = 485 nm was reported for 1,3-diphenylpropenylium tetrafluoroborate: Hafner, K; Pelster, H.; Angew. Chem. 1961, 73, 342.
24. -1): Strehlke, I. K., unpublished results; see also Ref. (1d).