Optimization of the microwave-assisted ortho ester claisen rearrangement: Application to monoterpenols

Synthetic Communications

Volumn 40, Issue 3, 2010, Pages 462-468

  Mehl, Florence ^a   Bombarda, Isabelle ^a   Franklin, Carine ^b   Gaydou, Emile M ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b Chemistry Department   (France)

Author keywords

Focused microwave; Johnson Claisen; Monoterpenol; Ortho ester rearrangement

Indexed keywords

ESTER DERIVATIVE; ETHYL 2 [2 METHYLENE 5 (PROP 1 EN 2 YL)CYCLOHEXYL]ACETATE; ETHYL 3,7 DIMETHYL 3 VINYLOCT 6 ENOATE; NEROL; PERILLYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; MICROWAVE RADIATION; REACTION TIME; SYNTHESIS;

EID: 73949090065     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902985515     Document Type: Article

References (14)

1. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T. T.; Faulkner, D. J.; Petersen, M. R. A simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds: Synthesis of squalene. J. Am. Chem. Soc. 1970, 92, 741-743.
2. (a) Claisen, L. Rearrangement of phenyl allyl ethers in C-allylphenols. Chem. Ber. 1912, 45, 3157-3166;
3. (b) Ziegler, F. E. The thermal, aliphatic Claisen rearrangement. Chem. Rev. 1988, 88, 1423-1452.
4. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2006.
5. Chemat-Djenni, Z.; Hamada, B.; Chemat, F. Atmospheric pressure microwave assisted heterogeneous catalytic reactions. Molecules 2007, 12, 1399-1409.
6. Hedidi, M.; Hamdi, S. M.; Mazari, T.; Boutemeur, B.; Rabia, C.; Chemat, F.; Hamdi, M. Microwave-assisted synthesis of calix[4]resorcinarenes. Tetrahedron 2006, 62, 5652-5655.
7. Roberts, B. A.; Strauss, C. R. Toward rapid, "green," predictable microwave-assisted synthesis. Acc. Chem. Res. 2005, 38, 653-661.
8. De la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Microwaves in organic synthesis: Thermal and non-thermal microwave effects. Chem. Soc. Rev. 2005, 34, 164-178.
9. Srikrishna, A.; Nagaraju, S.; Kondaiah, P. Application of microwave heating technique for rapid synthesis of c,d-unsaturated esters. Tetrahedron 1995, 51, 1809-1816.
10. Abramovitch, R. A. Applications of microwave energy in organic chemistry: A review. Org. Prep. Proc. Int. 1991, 23, 683-711
11. Tymoshenko, D. O. Microwave-assisted Claisen and aza-Claisen rearrangements. Mini-Rev. Org. Chem. 2008, 5, 85-95.
12. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry. J. Org. Chem. 2008, 73, 36-47.
13. Paruch, E.; Ciunik, Z.; Nawrot, J.; Wawrzenczyk, C. Lactones, 9: Synthesis of terpenoid lactones active insect antifeedants. J. Agric. Food Chem. 2000, 48, 4973-4977.
14. Günther, H. J.; Guntrum, E.; Jäger, V. Synthese von 4-Penten-4-oliden(c-Methylen-a-butyrolactonen) über 4-Pentensäuren. Lieb. Ann. Chem. 1984, 15-30.