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Volumn 121, Issue 13, 1999, Pages 3065-3071

Unusual [1,2]- and [1,3]-M(CO)5 shifts in Fischer carbene complexes: [4 + 3] and [3 + 3] annulation reactions of furan and pyrrole rings

Author keywords

[No Author keywords available]

Indexed keywords

DIAZEPINE DERIVATIVE; FURAN DERIVATIVE; IMINE; PYRROLE DERIVATIVE;

EID: 0033531667     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983692o     Document Type: Article
Times cited : (68)

References (81)
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    • We have recently found that the 1,2-addition of alkynyllithium reagents to Fischer aryl carbenes derived from menthol is followed by [1,3]-migration of the pentacarbonyltungsten fragment: Barluenga, J.; Trabanco, A. A.; Flórez, J.; García-Granda, S.; Llorca, M. A. J. Am. Chem. Soc. 1998, 120, 12129.
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    • For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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    • Aumann, R.1    Meyer, A.G.2    Frölich, R.3
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    • note
    • -1, F(000) = 1176, T = 293(2) K. Final conventional R = 0.074 (ωR2 = 0.1753) for 2745 "observed" reflections and 265 variables, GOF = 1.033.
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    • note
    • On the basis of this proposal, it was realized that ring expansion would occur if an imine derived from 2-aminomethylpyrrole were employed (see below): (matrix presented) Unfortunately, the reaction of the benzaldehyde imine with carbene 3 did not afford the corresponding pyrrolodiazepine, but only decomposition products were formed.
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    • (b) Unpublished results from our laboratory.
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    • note
    • Regarding the metal there are only minor variations, all related to yields, when shifting from chromium to tungsten complexes. This is in sharp contrast with our previous results in the cyclization reactions of simple 1-azadienes with alkynyl Fischer carbene complexes (see refs 4e and 22).


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