Review on non-thermal effects of microwave irradiation in organic synthesis

Journal of Microwave Power and Electromagnetic Energy

Volumn 41, Issue 1, 2007, Pages 44-64

  de la Hoz, Antonio ^a   Díaz Ortiz, Angel ^a   Moreno, Andrés ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Microwave; Non thermal effects; Organic synthesis; Thermal effects

Indexed keywords

ABSORPTION; HEATING RATE; MATHEMATICAL MODELS; RADIATION EFFECTS; SYNTHESIS (CHEMICAL);

NON-THERMAL EFFECTS; ORGANIC SYNTHESIS; POLAR SUBSTANCES; POLARIZED RADIATION;

MICROWAVE IRRADIATION;

EID: 37749029071     PISSN: 08327823     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (45)

1. Agrawal, D., Cheng, J. and Roy, R. (2002). "Radically Different Effects on Materials by Separated Microwave Electric and Magnetic Fields." Mat. Res. Innovat. 5, pp.170-177.
2. Berlan, J., Giboreau, P., Lefeuvre, S. and Marchand, C. (1991). "Synthèse Organique sous Champ Micro ondes: Premier Exemple d'Activation Spécifique en Phase Homogène." Tetrahedron Lett. 32, pp.2363-2366.
3. Berlan, J., Laurent, R., Laporterie, A., Dubac, J., Lefeuvre, S. and Audhuy, M. (1992)."Specific Activation by Microwaves: Myth or Reality?" J. Org. Chem. 57, pp.7099-7102.
4. Bogdal, D., Lukasiewicz, M. and Pielichowskia, J. (2003). "Microwave-Assisted Oxidation of Side Chain Arenes by Magtrieve™." Adv. Synth.Catal., 345, pp.1269-1272.
5. Bose, A. K., Banik, B. K. and Manhas, M. S. (1995). "Stereocontrol of Beta-Lactam Formation Using Microwave Irradiation." Tetrahedron Lett. 36, pp. 213-216.
6. Bose, A. K., Jayaramen, M., Okawa, A., Bari, S. S., Robb, E. W. and Manhas, M. S. (1996). "Microwave-Assisted Rapid Synthesis of α-Amino-β-Lactams." Tetrahedron Lett. 37, pp.6989-6992.
7. Collins, M. and Hayes, B. L. CEM Corporation NC, US Patent 6,744,024, June 1, 2004.
8. Cossío, F. P., Arrieta, A. and Lecea, B. (1998). "Origins of the Stereodivergent Outcome in the Staudinger Reaction between Acyl Chlorides and Imines." J. Org. Chem. 63, pp.5869-5876.
9. de la Hoz, A., Díaz-Ortiz, A. and Moreno, A. (2004) "Selectivity in Organic Synthesis Under Microwave Irradiation." Current Org. Chem. 8, pp.903-918.
10. N2 Reaction in a Microwave Field." J. Phys. Chem. A 106, pp.8516-8524.
11. Engman, L. and Ericsson, C. (2004). "Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds." J. Org. Chem. 69, pp.5143-5146.
12. 3-tetralrydropyridines Via Microwave-accelerated ring-closing Metathesis." Tetrahedron Lett. 44, pp. 4899-4901.
13. Hayes, B. L., (2002). Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC,.
14. Kappe, C. O., Garbacia, S., Desai, B. and Lavaster, O., (2003). "Microwave-Assisted Ring-Closing Metathesis Revisited. On the Question of the Nonthermal Microwave Effect." J. Org. Chem. 68, pp.9136-9139.
15. Kilburn, J. D., Lamberto, M. and Corbett, D. F. (2003). "Microwave Assisted Free Radical Cyclisation of Alkenyl and Alkynyl Isocyanides with Thiols." Tetrahedron Lett. 44, pp.1347-1349.
16. Klán, P. and Církva, V (2002). Microwave Photochemistry, in Microwaves in Organic Synthesis, ed. A. Loupy, Wiley-VCH, Weinheim, pp.463-486.
17. Langa, F., de la Cruz, P., de la Hoz, A., Díaz-Ortiz, A. and Díez-Barra, E. (1997). "Microwave Irradiation: More Than Just a Method for Accelerating Reactions." Contemp. Org. Synth. 4, pp.373-386.
18. Langa, F., de la Cruz, P., de la Hoz, A., Espíldora, E., Cossío, F. P. and Lecea, B. (2000). "Modification of Regioselectivity in Cycloadditions to C70 Under Microwave Irradiation." J. Org. Chem. 65, pp.2499-2507.
19. Larhed, M., Kaiser, N. F. K., Bremberg, U., Moberg, C. and Hallberg, A. (2000). "Fast, Convenient and Efficient Molibdenum-Catalyzed Asymmetric Allylic Alkylation Under Noninert Conditions: An example of Microwave Promoted Synthesis." Angew. Chem., Int. Ed. 39, pp.3595-3598.
20. Leadbeater, N. E., Pillsbury, S. J., Shanahan, E. and Williams, V. A. (2005). "An Assessment of the Technique of Simultaneous Cooling in Conjunction with Microwave Heating for Organic Synthesis." Tetrahedron 61, pp.3565-3585.
21. Lidström, P. (2003). "How Do Microwaves Speed Up Chemical Reactions." Personally Speaking, (2), pp. 11-13.
22. Loupy, A. and Perreux, L. (2001). "A Tentative Razionalization of Microwave Effects in Organic Synthesis According to the Reaction Medium and Mechanistic Considerations." Tetrahedron 57, pp. 9199-9223.
23. Loupy, A., Maurel, F. and Sabatié-Gogova, A. (2004). "Improvements in Diels-Alder Cycloadditions with Some Acetylenic Compounds Under Solvent-Free Microwave-assisted Conditions: Experimental Results and Theoretical Approaches." Tetrahedron 60, pp.1683-1691.
24. Loupy, A. Wiley-VCH, Weinheim ed (2002). Microwaves in Organic Synthesis.
25. Mason, T. J., Lorimer, J. P. (1988). Sonochemistry, Theory, Applications and Uses of Ultrasound in Chemistry, Ellis Horwood, Chichester.
26. Mayo, K. G., Nearhoof, E. H., Kiddle, J. J. (2002)."Microwave-Accelerated Ruthenium-Catalyzed Olefin Metathesis." Org. Lett. 4, pp.1567-1570.
27. Mingos, D. M. P. and Baghurst, D. R. (1992). "Superheating Effects Associated With Microwave Dielectric Heating." J. Chem Soc., Chem. Commun., pp. 674-677.
28. Mingos, D. M. P. and Whittaker A. G. (1995). Microwave Dielectric Heating Effects in Chemical Synthesis in Chemistry Under Extreme or Non Classical Conditions, John Wiley & Sons. pp.479-545.
29. Mingos, D. M. P. Gabriel, C. Gabriel, S., Grant, E. H. and Halstead, B. S. J. (1998). "Dielectric Parameters Relevant to Microwave Dielectric Heating." Chem. Soc. Rev. 27, pp.213-224.
30. Mingos, D. M. P. Zhang, X. and Hayward, D. O., (1999). "Apparent Equilibrium Shifts and Hot-spot Formation for Catalytic Reactions Induced by Microwave Dielectric Heating." Chem. Commun. pp.975-976.
31. Ondruschka, B., Nüchter, M., Müller, U., Tied, A. and Lautenschlager, W. (2003). "Microwave Assisted Chemical Reactions." Chem. Eng. Technol., 26, pp. 1207-1216.
32. Pagnotta, M., Pooley, C. L. F., Gurland, B. and Choi, M. (1993). "Microwave Activation of the Mutarotation of Alpha-D-Glucose - an Example of an Intrinsic Microwave Effect." J. Phys. Org. Chem. 6, pp.407-411.
33. Ritter, H., Iannelli, M. and Alupei, V. (2005). "Selective Microwave-accelerated Synthesis and Polymerization of Chiral Methacrylamide Directly from Methacrylic Acid and (R)-1-phenyl-ethylamine." Tetrahedron 61, pp.1509-1515.
34. Schanche, J.-S. (2003). "Microwave Synthesis Solutions from Personal Chemistry." Molecular Diversity, 7, pp.291-298.
35. Strauss, C. R., Raner, K. D., Vyskoc, F. and Mokbel, L. (1993). "A Comparison of Reaction Kinetics Observed under Microwave Irradiation and Conventional Heating." J. Org. Chem. 58, pp.950-953.
36. Strauss, C. R. and Trainor, R. W. (1995). "Developments in Microwave-Assisted Organic Chemistry." Aust. J. Chem., 48, pp.1665-1692.
37. Stuerga, D. A. C. and Gaillard, P. (1996). "Microwave Heating as a New Way to Induce Localized Enhancements of Reaction Rate. Non-Isothermal and Heterogeneous Kinetics." Tetrahedron. 52, pp.5505-5510.
38. Stuerga, D. A. C. and Gaillard, P. (1996). "Microwave Athermal Effects in Chemistry: A Myth's Autopsy Part I: Historical Background and Fundamentals of Wave-matter Interaction." J. Microwave Power Electromagn. Energy 31, pp.87-100.
39. Stuerga, D. A. C. and Gaillard, P. (1996). "Microwave Athermal Effects in Chemistry: A Myth's Autopsy Part II: Orienting Effects and Thermodynamic Consequences of Electric Field." J. Microwave Power Electromagn. Energy 31, pp.101-113.
40. Tanaka, Y., Watanabe, M., Suzuki H., Ishida, T., Oshikawa, T. and Tori, A. (2004). "One-Pot Synthesis of Helical Aromatics: Stereoselectivity, Stability Against Racemization, and Assignment of Absolute Configuration Assisted by Experimental and Theoretical CircularDichroism." J. Org. Chem. 69, pp.7794-7801.
41. Tanimoto, Y., Mukai, M. and Fujiwara, Y. (1993). "Product Yield-Detected ESR Studies of Photochemical-Reaction of a Bifunctional Chain Molecule - Magnetic-Field and Microwave Effects." Z. Phys. Chem. 180, pp.223-233.
42. Varma, R. S. (2003). Microwave Technology-Chemical Synthesis Applications in Kirk-Othmer Encyclopedi of Chemical Technology, J. Wiley & Sons, Inc.
43. Varma, R. S., Jachuck, R. J. J. and Selvaraj, D. K. (2006). "Process Intensification: Oxidation of Benzyl Alcohol Using a Continuous Isothermal Reactor Under Microwave Irradiation." Green Chem. 8, pp.29-33.
44. Wasielewski, M. R., Bock, C. H., Bowman, M. K. and Norris, J. R. (1983). "Controlling the Duration of Photosynthetic Charge Separation with Microwave Radiation." Nature 303, pp.520-522.
45. Zhang, Z., Zhou, L., Zhang, M., Wu, H. and Chen, Z.G. (2001). "One Billionhertz Microwave Athermal Action on the Synthesis of Aromatic Esters at Normal Pressure." Synth. Commun. 31,pp.243-2439.