Reactivity of carbanions of Fischer-type carbene complexes with pyrylium salts. Synthesis and characterization of new γ-methylenepyran carbene complexes via an addition-oxidation-deprotonation process

Tetrahedron

Volumn 58, Issue 37, 2002, Pages 7519-7530

  Caro, Bertrand ^a   Le Poul, Pascal ^a   Robin Le Guen, Françoise ^a   Saillard, Jean Yves ^b   Kahlal, Samia ^b   Moinet, Claude ^b   Le Poul, Nicolas ^c   Vaissermann, Jacqueline ^d  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITY OF EXETER   (United Kingdom)

^d CNRS   (France)

Author keywords

DFT calculations; Methylenepyran Fischer type carbene complexes; Pyrylium salts; Tungsten and chromium carbenes

Indexed keywords

CARBENOID; HETEROCYCLIC COMPOUND; PYRYLIUM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CALCULATION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS; X RAY ANALYSIS;

EID: 0037048502     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00800-1     Document Type: Article

References (59)

1. Balaban A.T., Dinculescu A., Dorofeenko G.N., Mezheritskii V.V., Kobik A.V., Fischer, G.W. In Pyrylium Salts: Syntheses, Reactions and Physical Properties. Advances in Heterocyclic Chemistry, Katrisky, A.R., Ed.; Academic: New York, 1982; Suppl. 2.
2. Taylor R.J.K., Hemming K., De Medeiros E.F. J. Chem. Soc. Perkin. Trans. 1. 1995;2385.
3. (a) Dimroth K., Neubeauer G. Chem. Ber. 99:1966;399
4. (b) Dimroth K., Neubeauer G. Chem. Ber. 92:1959;2042
5. (c) Dimroth K., Neubeauer G. Angew. Chem. 69:1957;95.
6. Le Poul P., Robin-Le Guen F., Senechal-Tocquer M.C., Caro B. J. Organomet. Chem. 545-547:1997;447.
7. Furber M., Herbert J.M., Taylor R.J.K. J. Chem. Soc. Perkin. Trans 1. 1989;683.
8. (a) Dimroth K., Wolf K.H. Angew. Chem. 21:1960;777
9. (b) Ostensen E.T., Undheim K. Acta. Chem. Scand. 6:1973;2184.
10. Dötz K.H., Fischer H., Hofmann P., Kreissl F.R., Schubert U., Weiss K. Transition Metal Carbene Complexes. 1983;Verlag Chemie, Weinheim.
11. (a) Bernasconi C.F., Leyes A.E. J. Am. Chem. Soc. 119:1997;5169
12. (b) Casey C.P., Anderson L.A. J. Am. Chem. Soc. 96:1974;1230
13. (c) Casey C.P., Brunsvold W.R. J. Organomet. Chem. 118:1976;309
14. (d) Gandler J.R., Bernasconi C.F. Organometallics. 8:1989;2282.
15. (a) Xu Y.C., Wulf W.D. J. Org. Chem. 52:1987;3263
16. (b) Schmeck C., Hegedus L.S. J. Am. Chem. Soc. 116:1994;9927
17. (c) Chelain E., Parlier A., Audouin M., Rudler H., Daran J.C., Vaissermann J. J. Am. Chem. Soc. 115:1993;10568
18. (d) Anderson B.A., Wulf W.D., Rahm A. J. Am. Chem. Soc. 115:1993;4602
19. (e) Casey C.P., Brunsvold W.R. Inorg. Chem. 16:1977;391
20. (f) Baldoli C., Del Buttero P., Licandro E., Maiorana S., Papagni A., Zanotti-Gerosa A. Tetrahedron Lett. 34:1994;6377
21. (g) Streubel R., Hoblod M., Jeske J., Jones P. J. Chem. Soc., Chem. Commun. 1994;2457
22. (h) Sierra M. Chem. Rev. 100:2000;3591
23. (i) Barluenga J., Florez J., Fananas F.J. J. Organomet. Chem. 624:2001;5
24. (j) Aumann R. Eur. J. Org. Chem. 2000;17
25. (k) Dötz K.H., Gomes da Silva E. Tetrahedron. 56:2000;8291
26. (l) Herndon J.W. Tetrahedron. 56:2000;1257.
27. For a preliminary communication of a part of this work see: Caro B., Le Poul P., Robin-Le Guen F., Senechal-Tocquer M.C. Tetrahedron Lett. 39:1998;557.
28. Strzelecka H., Grom V., Signand G., Veber M., Jallabert C. Mol. Cryst. Liq. Cryst. 137:1986;373.
29. Aumann R. Chem. Ber. 125:1992;1141.
30. Cosset C., Del. Rio I., Le Bozec H. Organometallics. 14:1995;1938.
31. (a) Licandro E., Maiorana S., Papagni A., Zanotti-Gerosa A., Cariati F., Bruni S., Moret M., Chiesi Villa A. Inorg. Chim. Acta. 1994;233
32. (b) Aumann R., Meyer A.G., Frölich R. J. Am. Chem. Soc. 118:1996;10853
33. (c) Caro B., Le Poul P., Robin-Le Guen F., Senechal-Tocquer M.C., Saillard J.Y., Kahlal S., Ouahab L., Gohlen S. Eur. J. Org. Chem. 2000;577.
34. Belsky I., Dodiuk H., Shvo Y. J. Org. Chem. 39:1974;989.
35. Lattuada L., Licandro E., Papagni A., Maiorana S. J. Chem. Soc., Chem. Commun. 1988;1092.
36. Mills O.S., Redhouse A.O. Angew. Chem., Int. Ed. Engl. 4:1965;1082.
37. Turowska-Tyrk L., Krygowsky T.M., Milart P. J. Mol. Struct. 263:1991;235.
38. Maliska K.L., Top S., Vaissermann J., Caro B., Senechal-Tocquer M.C., Saillard J.Y., Triki S., Kahlal S., Butten J.F., Mc Glinchey M.J., Jaouen G. Organometallics. 14:1995;5273.
39. Ohe K., Miki K., Yokoi T., Nishino F., Uemura S. Organometallics. 19:2000;5525.
40. (a) Casey C.P., Albin L.D., Saeman M.C., Evans D.H. J. Organomet. Chem. 155:1978;C37-C40
41. (b) Krusic P.J., Klabunde U., Casey C.P., Block T.F. J. Am. Chem. Soc. 98:1976;2015.
42. (a) Lloyd M.K., McCleverty J.A., Orchard D.G., Connor J.A., Hall M.B., Hillier I.H., Jones E.M., McEwen G.K. J. Chem. Soc. Dalton Trans. 1973;1743
43. (b) Jayaprakash K.N., Ray P.C., Matsuoka I., Bhadbhade M.M., Puranik V.G., Das P.K., Nishihara H., Sarkar A. Organometallics. 18:1999;3851.
44. Robin-Le Guen F., Le Poul P., Caro B., Pichon R., Kervarec N. J. Organomet. Chem. 626:2001;37.
45. Israel D.L., Marks T.J., Ratner M.A. J. Am. Chem. Soc. 120:1998;11174.
46. Sierra A.S., Del Amo J.C., Mancheno M.J., Gomez-Gallego M. J. Am. Chem. Soc. 123:2001;854.
47. Perrin D.D., Armarego W.L.F., Perrin D.R. Purification of Laboratory Chemicals. 1980;Pergamon, New York.
48. Watkin D.J., Carruthers J.R., Betteridge P.W. CRYSTALS User's Guide, Chemical Crystallography. 1985;University of Oxford, UK.
49. Amsterdam Density Functional (ADF) Program, Version 2.3; Vrije Universteit: Amsterdam, The Netherlands, 1996.
50. (a) Baerends E.J., Ellis D.E., Ros P. Chem. Phys. 2:1973;41
51. (b) Baerends E.J., Ros P. Int. J. Quantum. Chem. S12:1978;169
52. (c) Boerrigter P.M., te Velde G., Baerends E.J. Int. J. Quantum Chem. 33:1988;87
53. (d) te Velde G., Baerends E.J. J. Comput. Phys. 99:1992;84.
54. Vosko S.D., Wilk L., Nusair M. Can. J. Chem. 58:1990;1200.
55. (a) Becke A.D. J. Chem. Phys. 84:1986;4524
56. (b) Becke A.D. Phys. Rev. A. 38:1988;3098.
57. Perdew J.P. Phys. Rev. B. 33:1986;8882
58. Perdew J.P. Phys. Rev. B. 34:1986;7406.
59. Verluis L., Ziegler T. J. Chem. Phys. 322:1988;88.