Domino pericyclic reactions of acyclic conjugated (E,Z,E,E)-tetraenes

Tetrahedron Letters

Volumn 48, Issue 18, 2007, Pages 3281-3284

  Skropeta, Danielle ^a,b   Rickards, Rodney W ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

Electrocyclic reaction; Intramolecular Diels Alder reaction; Polyenes; Tetraenes

Indexed keywords

5 VINYL 1,3 CYCLOHEXADIENE; ALKENE DERIVATIVE; TRICYCLO[3.2.1.0]OCT 3 ENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIELS ALDER REACTION; LYSIS; THERMAL ANALYSIS;

ALNUS;

EID: 34047183626     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.011     Document Type: Article

References (25)

1. Woodward R.B., and Hoffmann R. J. Am. Chem. Soc. 87 (1965) 395
2. Huisgen R., Dahmen A., and Huber H. J. Am. Chem. Soc. 89 (1967) 7130
3. Marvell E.N. Thermal Electrocyclic Reactions (1980), Academic Press, New York pp 376-401
4. Okamura W.H., and de Lera A.R. 1,3-Cyclohexadiene Formation Reactions. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford 743-745
5. Morwick T.M., and Paquette L.A. J. Org. Chem. 62 (1997) 627
6. Marvel E.N., Seubert J., Vogt G., Zimmer G., Moy G., and Siegmann J.R. Tetrahedron 34 (1978) 1323
7. Roth W.R., and Peltzer B. Liebigs Ann. 685 (1965) 56
8. ten Have R., and van Leusen A.M. Tetrahedron 54 (1998) 1913
9. Loeliger P., and Mayer H. Helv. Chim. Acta 63 (1980) 1604
10. For examples of intramolecular Diels-Alder reactions of 5-vinyl-1,3-cyclohexadienes see:. Giomi D., Nesi R., Turchi S., and Mura E. J. Org. Chem. 65 (2000) 360
11. Ng S.M., Beaudry C.M., and Trauner D. Org. Lett. 5 (2003) 1701
12. Abad A., Agulló C., Cuñat A.C., de Alfonso I., Navarro I., and Vera N. Molecules 9 (2004) 287
13. D'Souza D.M., Rominger F., and Müller T.J.J. Chem. Commun. (2006) 4096
14. Rickards R.W., and Skropeta D. Tetrahedron 58 (2002) 3793
15. spartan sg1, version 5.0.1, Open GL; Wavefunction Inc: California, 1991-1997.
16. 2,7]oct-3-enes 3a-c are available as Supplementary data.
17. All new compounds gave satisfactory spectral and analytical data. Selected spectral data for compounds 1a, 3a, 3b and 3c are available as Supplementary data.
18. R = 11.89, 11.98 min).
19. One other product was detected by GC in ∼5% yield, however, its retention time differed to that of the tricylic product by only 0.1 min and the two products were inseparable; their close retention times suggest they are isomeric.
20. Zimmerman H.E., Grunewald G.L., Paufler R.M., and Sherwin M.A. J. Am. Chem. Soc. 91 (1969) 2330
21. CS Chem-3D Pro., Version 3.1 for Apple Macintosh; CambridgeSoft Corporation: Cambridge, 1995.
22. R = 11.69, 11.89 min).
23. Two minor products (<5% yield) were also detected by GC.
24. Bohlmann F., Jakupovic J., Ahmed M., Grenz M., Suding H., Robinson H., and King R.M. Phytochemistry 20 (1981) 113
25. Pelletier S.W., Djarmati Z., and Mody N.V. Tetrahedron Lett. 21 (1976) 1749