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

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 557-560

  Caro, Bertrand ^a   Le Poul, Pascal ^a   Guen, Françoise Robin Le ^a   Sénéchal Tocquer, Marie Claude ^a   Vaisserman, Jacqueline ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ION; PYRAN DERIVATIVE;

ARTICLE; COMPLEX FORMATION; OXIDATION; POLYMERIZATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0032510095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10683-9     Document Type: Article

References (17)

1. 1. Barton, A.T.; Fischer, G. W.; Dinculescu, A.; Koblick, A. V.; Dorofeenko, G. N.; Mezheritskii, V. V.; Schroth, W. Pyrylium salts: syntheses, reaction and physical properties ; advances in heterocyclic chemistry, suppl.II ; A. R. Katrisky Ed.; Academic Press: New York, 1982.
2. 2. See for example: Anderson, B. A.; Wulff, W. D.; Rahm, A. J. Am. Chem. Soc. 1993, 115, 4562-4611.
3. 3. Cosset, C.; Del Rio, I.; Le Bozec, H. Organometallics 1995, 14, 1938-1944.
4. 4. Macomber, D. W.; Liang, M.; Rogers, R. D. Organometallics 1988, 7, 416-422.
5. 5. Wulff, W. D.; Tang, P. C.; Chan, K. S.; McCallum, J. S.; Yang, D. C.; Gilberton, S. R. Tetrahedron 1985, 24, 5813-5832.
6. 6. For the synthesis and properties of 4H-methylenepyran substituted by electron withdrawing group, see: Shvo, Y.; Dodink, H.; Belsky, I. J. Org. Chem. 1974, 39, 983-995.
7. CH = 160Hz) ; 132.142 (s) ; 136.718(s) ; 137.841 (s) ; 155.763 (s) ; 158.945 (s) ; 199.258 (s) ; 204.93 (s) ; 286.072 (s).
8. 8. Strzelecka, H.; Gioms, V.; Sigand, G.; Veber, M.; Jallabert, C. Mol. Cryst. Liq. Cryst. 1986, 137, 373-379.
9. 9. Complementary works will be necessary to find the origin of this lack of reactivity.
10. HH = 1.81Hz) ; 7.4-7.6 (m, 6H) ; 7.8-8 (m, 4H) ; 10,.4 (s, 1H).
11. 3, MoKα radiation (λ = 0,71069Å).
12. 12. For a discussion relating to the pyrylium-pyran characters in pyran-2-ylidene complexes, see: Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10553-10661.
13. 3.
14. 14. For a similar effect in (alkoxyenamino carbene) chromium complexes, see: Lattuada, L.; Licandro, E.; Pagagni, A.; Maiorana, S. J. Chem. Soc. ; Chem. Commun. 1988, 1092-1093.
15. 15. Mills, O. S.; Redhouse, A. O. Angew. Chem. Int. Ed. Engl. 1965, 4, 1082.
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17. 17. Malisza, K. L.; Top, S.; Vaisserman, J.; Caro, B.; Sénéchal-Tocquer, M.C.; Sénéchal, D.; Saillard, J. Y.; Triki, S.; Kahlal, S.; Butten, J.F.; McGlinchey, M. J.; Jaouen, G. Organometallics 1995, 14, 5273-5280.