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Volumn 62, Issue 26, 1997, Pages 9229-9235

Fischer Carbene Complexes in Heterocyclic Synthesis. Selective Cycloaddition Reactions to 2-Aza-1,3-butadienes

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EID: 0000638898     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715074     Document Type: Article
Times cited : (55)

References (70)
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    • For previous examples from our laboratory, see ref 4e, p 20
    • For previous examples from our laboratory, see ref 4e, p 20.
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    • note
    • 2 = t-Bu) gives none of the corresponding 16b,c.
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    • Reviews on azepines, see: (a) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131. (b) Hassenrück, K.; Martin, H. D. Synthesis 1988, 569. Smalley, R. K. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 491. For recent syntheses of 2-azepinones, see: (d) Robl, J. A.; Cimarusti, M. P. Tetrahedron Lett. 1994, 35, 1393. (e) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348. (f) Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1 1994, 3397. (g) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131.
    • (1991) Tetrahedron , vol.47 , pp. 9131
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    • note
    • Using chromium carbene complexes resulted in all cases in the formation of complex mixtures of unidentified products. In the same way, all attempts to carry out the [4 + 3] cycloaddition with αβ-unsaturated molybdenum carbene complexes, e.g. pentacarbonyl[(1-cyclohexenyl) methoxymethylene]molybdenum(0), at 25 and 60°C led to recovery of the starting materials and to products derived from decomposition of the carbene complex, respectively.


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