Collect. Czech. Chem. Commun. 2006, 71, 667-678
https://doi.org/10.1135/cccc20060667

Intensification of a Reaction by the Addition of a Minor Amount of Solvent: Diels-Alder Reaction of 2H-Pyran-2-ones with Alkynes

Krištof Kranjc and Marijan Kočevar*

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, SI-1000 Ljubljana, Slovenia

References

1a. Sheldon R. A.: Green Chem. 2005, 7, 267. <https://doi.org/10.1039/b418069k>
1b. Matlack A.: Green Chem. 2003, 5, G7.
1c. Trost B. M.: Acc. Chem. Res. 2002, 35, 695. <https://doi.org/10.1021/ar010068z>
1d. Anastas P. T., Kirchhoff M. M.: Acc. Chem. Res. 2002, 35, 686. <https://doi.org/10.1021/ar010065m>
2a. Adams D. J., Dyson P. J., Tavener S. J.: Chemistry in Alternative Reaction Media. Wiley, New York 2004.
2b. Tanaka K.: Solvent-Free Organic Synthesis. Wiley-VCH, Weinheim 2003.
2c. Wasserscheid P., Welton T. (Eds): Ionic Liquids in Synthesis. Wiley-VCH, Weinheim 2003.
2d. Jessop P. G., Leitner W. (Eds): Chemical Synthesis Using Supercritical Fluids. Wiley-VCH, Weinheim 1999.
2e. Li C.-J., Chan T.-H.: Organic Reactions in Aqueous Media. Wiley, New York 1997.
2f. Grieco P. A. (Ed.): Organic Synthesis in Water. Blackie Academic and Professional, London 1998.
3a. Loupy A. (Ed.): Microwaves in Organic Synthesis. Wiley-VCH, Weinheim 2002.
3b. Hayes B. L.: Microwave Synthesis: Chemistry at the Speed of Light. CEM Publishing, Matthews (NC) 2002.
3c. Lidström P., Tierney J., Wathey B., Westman J.: Tetrahedron 2001, 57, 9225. <https://doi.org/10.1016/S0040-4020(01)00906-1>
3d. Varma R. S.: Green Chem. 1999, 1, 43. <https://doi.org/10.1039/a808223e>
3e. Nüchter M., Ondruschka B., Bonrath W., Gum A.: Green Chem. 2004, 6, 128. <https://doi.org/10.1039/b310502d>
3f. Kappe C. O.: Angew. Chem., Int. Ed. 2004, 43, 6250. <https://doi.org/10.1002/anie.200400655>
3g. de la Hoz A., Díaz-Ortiz A., Moreno A.: Chem. Soc. Rev. 2005, 34, 164. <https://doi.org/10.1039/b411438h>
4a. Afarinkia K., Vinader V., Nelson T. D., Posner G. H.: Tetrahedron 1992, 48, 9111. <https://doi.org/10.1016/S0040-4020(01)85607-6>
4b. Woodard B. T., Posner G. H. in: Advances in Cycloaddition (M. Harmata, Ed.), Vol. 5, p. 47. JAI Press Inc., Greenwich 1999.
4c. Shusherina N. P.: Russ. Chem. Rev. 1974, 43, 851. <https://doi.org/10.1070/RC1974v043n10ABEH001867>
5a. Kranjc K., Leban I., Polanc S., Kočevar M.: Heterocycles 2002, 58, 183.
5b. Kranjc K., Polanc S., Kočevar M.: Org. Lett. 2003, 5, 2833. <https://doi.org/10.1021/ol034852q>
5c. Kranjc K., Štefane B., Polanc S., Kočevar M.: J. Org. Chem. 2004, 69, 3190. <https://doi.org/10.1021/jo035473d>
5d. Kranjc K., Kočevar M.: New J. Chem. 2005, 29, 1027. <https://doi.org/10.1039/b504852d>
6a. Kepe V., Kočevar M., Polanc S., Verček B., Tišler M.: Tetrahedron 1990, 46, 2081. <https://doi.org/10.1016/S0040-4020(01)89774-X>
6b. Vraničar L., Polanc S., Kočevar M.: Tetrahedron 1999, 55, 271. <https://doi.org/10.1016/S0040-4020(98)01032-1>
6c. Kepe V., Kočevar M., Petrič A., Polanc S., Verček B.: Heterocycles 1992, 33, 843.
6d. Kepe V., Kočevar M., Polanc S.: J. Heterocycl. Chem. 1996, 33, 1707. <https://doi.org/10.1002/jhet.5570330626>
7a. Li C.-J.: Chem. Rev. 2005, 105, 3095. <https://doi.org/10.1021/cr030009u>
7b. Leadbeater N. E., Marco M.: Angew. Chem., Int. Ed. 2003, 42, 1407. <https://doi.org/10.1002/anie.200390362>
7c. Arvela R. K., Leadbeater N. E.: Org. Lett. 2005, 7, 2101. <https://doi.org/10.1021/ol0503384>
7d. Ju Y., Varma R. S.: Org. Lett. 2005, 7, 2409. <https://doi.org/10.1021/ol050683t>
7e. Miyazawa A., Tanaka K., Sakakura T., Tashiro M., Tashiro H., Prakash G. K. S., Olah G. A.: Chem. Commun. 2005, 2104. <https://doi.org/10.1039/b500541h>
7f. Ju Y., Varma R. S.: Tetrahedron Lett. 2005, 46, 6011. <https://doi.org/10.1016/j.tetlet.2005.07.018>
7g. Martelanc M., Kranjc K., Polanc S., Kočevar M.: Green Chem. 2005, 7, 737. <https://doi.org/10.1039/b508446f>
7h. Kremsner J. M., Kappe C. O.: Eur. J. Org. Chem. 2005, 3672. <https://doi.org/10.1002/ejoc.200500324>
7i. Leadbeater N. E.: Chem. Commun. 2005, 2881. <https://doi.org/10.1039/b500952a>
8a. Loupy A.: C. R. Chim. 2004, 7, 103. <https://doi.org/10.1016/j.crci.2003.10.015>
8b. Varma R. S.: Tetrahedron 2002, 58, 1235. <https://doi.org/10.1016/S0040-4020(01)01216-9>
8c. Varma R. S.: Pure Appl. Chem. 2001, 73, 193. <https://doi.org/10.1351/pac200173010193>
8d. Raunak, Kumar V., Mukherjee S., Poonam, Prasad A. K., Olsen C. E., Schäffer S. J. C., Sharma S. K., Watterson A. C., Errington W., Parmar V. S.: Tetrahedron 2005, 61, 5687. <https://doi.org/10.1016/j.tet.2005.03.027>
8e. Pinto D. C. G. A., Silva A. M. S., Brito C. M., Sandulache A., Carrillo J. R., Prieto P., Díaz-Ortiz A., de la Hoz A., Cavaleiro J. A. S.: Eur. J. Org. Chem. 2005, 2973. <https://doi.org/10.1002/ejoc.200500073>
8f. Dandia A., Arya K., Sati M., Gautam S.: Tetrahedron 2004, 60, 5253. <https://doi.org/10.1016/S0040-4020(04)00548-4>
8g. Loupy A., Maurel F., Sabatié-Gogová A.: Tetrahedron 2004, 60, 1683. <https://doi.org/10.1016/j.tet.2003.11.042>
8h. Pospíšil J., Potáček M.: Eur. J. Org. Chem. 2004, 710. <https://doi.org/10.1002/ejoc.200300481>
8i. Ješelnik M., Varma R. S., Polanc S., Kočevar M.: Green Chem. 2002, 4, 35. <https://doi.org/10.1039/b108029f>