Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 1062-1065

  Anaç, Olcay ^a   Sezer, Özkan ^a   Candan, Özlem ^a   Güngör, Füsun Şeyma ^a   Cansever, M Şerif ^a  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

1,5 Electrocyclization; 1,7 Electrocyclization; Carbene; Dihydrobenzoxepine; Dihydrofuran

Indexed keywords

ALPHA BENZYLIDENE BETA DICARBONYL DERIVATIVE; BENZOXEPIN DERIVATIVE; CARBONYL DERIVATIVE; DIHYDROBENZOXEPINE DERIVATIVE; DIHYDROFURAN DERIVATIVE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRESS; CYCLIZATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 37849035612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.197     Document Type: Article

References (22)

1. Anaç O., and Daut A. Liebigs Ann. Recl. (1997) 1249-1254
2. Anaç O., Daut-Özdemir A., and Sezer O. Helv. Chim. Acta 86 (2003) 290-297
3. Anaç O., Güngör F.S., Kahveci C., and Cansever M.S. Helv. Chim. Acta 87 (2004) 408-415
4. Anaç O., Güngör F.S., and Merey G. Helv. Chim. Acta 89 (2006) 1231-1240
5. Hamaguchi M., Matsubara H., and Nagai T. J. Org. Chem. 66 (2001) 5395-5404
6. Sliwinska A., and Warkentin J. Org. Lett. 9 (2007) 2605-2607
7. Charette A.B., Janes M.K., and Lebel H. Tetrahedron: Asymmetry 14 (2003) 867-872
8. Miller J.A., Jin W., and Nguyen S.T. Angew. Chem., Int. Ed. 41 (2002) 2953-2956
9. Aggarwal V.K., Alonso E., Fang G., Ferraro M., Hynd G., and Porcelloni M. Angew. Chem., Int. Ed. 40 (2001) 1433-1436
10. Schinnerl M., Böhm C., Seitz M., and Reiser D. Tetrahedron: Asymmetry 14 (2003) 765-771
11. Temme O., Taj S.A., and Anderson P.G. J. Org. Chem. 63 (1998) 6007-6015
12. Padwa A., Precedo L., and Semones M.A. J. Org. Chem. 64 (1999) 4079-4088
13. Padwa A., Boonsombat P., Rashatasakhon P., and Willis J. Org. Lett. 7 (2005) 3725-3727
14. Çelik M.A., Yurtsever M., Tüzün N.S., Güngör F.S., Sezer O., and Anaç O. Organometallics 26 (2007) 2978-2985
15. Güngör F.S., Anaç O., and Sezer O. Tetrahedron Lett. 48 (2007) 4883-4886
16. Maas G., and Müller A.. J. Prakt. Chem. 340 (1998) 315-322
17. Ethyl acetobenzylidene acetate was obtained as a mixture of Z and E isomers (1.90:1) after distillation. After chromatographic separation, the structures of the E- and Z-isomers were clarified from their NOESY spectra.
18. We determined that (E)-1b was only partially (ca. 10%) converted to (Z)-1a at room temperature after seven months. Refluxing pure (Z)-1a in benzene for 5 h also resulted in negligible amounts of conversion. Besides, the 65:35 Z/E ratio observed after the distillation in the synthetic procedure also indicates that the starting compound alone did not exhibit a facile Z to E conversion.
19. Huisgen R. Angew. Chem., Int. Ed. Engl. 19 (1980) 947-1034
20. Zecchi G. Synthesis (1991) 181-188
21. Eberbach W., Hadicke E., and Trostmann U. Tetrahedron Lett. 22 (1981) 4953-4956
22. Preliminary geometry optimization studies suggested that the probable structure C was significantly more stable than structure D in Scheme 2, whereas structures A and B in Scheme 2 had just about the same energies.