Access to the Bicyclo[5.3.1]undecadiene Ring System by Two Carbon Ring Enlargement of Bicyclo[3.3.1]nonane Derivatives

Synlett

Volumn 1996, Issue 4, 1996, Pages 385-386

  Miesch, Michel ^a   Mislin, Gaëtan ^a   Franck Neumann, Michel ^a  

^a CNRS   (France)

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Indexed keywords

EID: 0002635364     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5414     Document Type: Article

References (22)

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7. a. Clark, R.D.; Untch, K.G. J. Org. Chem., 1979, 44, 248-253 ; ibid J. Org. Chem., 1979, 44, 253 -
8. a. Clark, R.D.; Untch, K.G. J. Org. Chem., 1979, 44, 248-253 ; ibid J. Org. Chem., 1979, 44, 253 -
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11. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrel, R. J. Am. Chem. Soc., 1963, 85, 207.
12. The addition of enamine 2 with ethyl propynoate gives a complex mixture. We were able to isolate enaminoester 4 only in 20 % yield and the sole other product that we were able to identify results from an addition of morpholine (liberated during hydrolysis) with ethyl propynoate.
13. 3: 3.78 ppm (6H, s) ;Compound 6 : CH-CH=C(E) : 2.72 ppm (1H, bd, J = 10.2 Hz); CH=C(E) : 6.99 (1H, d, J = 1.0 Hz).
14. Egberink, R.J.M.; Verboom, W.; Benders, P.H.; Harkema, S.; Reinhoudt, D.N. Recl. Trav. Chim. Pays Bas, 1988, 107, 388.
15. 3) : 180, 173, 170, 167, 141, 128, 99, 98, 70, 69, 52, 52, 38, 33, 32, 30, 25,25, 25, 22 ; Anal. : Calc. % H 6.89, % C 60.26 - Found % H 6.64, % C 60.28.
16. Frew, A.J.; Proctor, G.R. J. C. S. Perkin Trans I, 1980, 1245; Frew, A.J.; Proctor, G.R.; Silverton, J.V. J.C.S. Perkin Trans I, 1980, 1251. McHugh, M.; Proctor, G.R. J. Chem. Res. (M) 1984, 2228.
17. Frew, A.J.; Proctor, G.R. J. C. S. Perkin Trans I, 1980, 1245; Frew, A.J.; Proctor, G.R.; Silverton, J.V. J.C.S. Perkin Trans I, 1980, 1251. McHugh, M.; Proctor, G.R. J. Chem. Res. (M) 1984, 2228.
18. Frew, A.J.; Proctor, G.R. J. C. S. Perkin Trans I, 1980, 1245; Frew, A.J.; Proctor, G.R.; Silverton, J.V. J.C.S. Perkin Trans I, 1980, 1251. McHugh, M.; Proctor, G.R. J. Chem. Res. (M) 1984, 2228.
19. Lamm, B.; Aurell, C.J. Acta Chem. Scand. B, 1982, 435.
20. Abou-Elzahab, M.M.; Ayyad, S.N.; Zimaity, M.T. Z. Naturforsch. 1986, 41b, 363.
21. More recently, this methodology was used for the ring expansion of cyclic β-ketophosphonates : Ruder, S.M.; Kulkarni, V.R. J. Org. Chem. 1995, 60, 3084.
22. The presence of the Michael adduces 11 was not detected in this case.