STUDY OF INFLUENCE THE TEMPERATURE ON THE REACTION OF DIENESYNTHESIS OF MONOESTERS OF NORBORNENDICARBONIC ACID ON THE TOTAL AND OPTICAL YIELD OF THE ADDUCT
Keywords:
cyclopentadiene, diene synthesis, monoesters of maleic acid, norbornenedicarboxylic acidAbstract
The influence of temperature of Diels-Alder reaction between cyclopentadiene and monoesters of maleic acid to the yield of obtained adducts has been studied. The optimum conditions of reaction have been founded. It is showed that at low temperatures the total yield of adduct has been decreased, but its optically yield increased. The increasing of temperature lead to increasing of total yield. But optically yield is decrase.
References
[1] Seguchi K., Sera R., Otsuki Y. An investigation of the endo product selectivity in the Diels-Alder reaction // Bulletin of the Chemical Society of Japan, 1975. Vol. 48, N 12. P. 36413644.
[2] Gbaguidi T., Kassehin U., Prevast J. Insight into the Diels-Alder reaction – a green chemistry revisitattion of the synthesis of a cantharidine-liketrypanocidal pilot-molecule // J. of Chemical and Pharnaceutical Reseach. 2015. Vol. 10. P. 172-174.
[3] Knall A-C., Hollauf M., Slugovc C. Kinetic studies of inverse electron demand DielsAlder reactions of norbornenes and 5,6-di-pyridin-2-yl-1,2,4,5-tetrazine // Tetrahedron Letters. 2014. Vol. 55, N 34. P. 4763-4766.
[4] Silbert E. Solvent effects in the Diels-Alder reaction: Dissert. candidate work. USA, 2002. 124 p.
[5] Gieling R., Klunder A. Immobilized cyclopentadiene in the Diels-Alder/retro Diels-Alder concept // ARKIVOC. 2004. N 2. P. 91-108.
[6] Zhang Z., Oeng Z-W., Hao M. Mechanochemical Diels-Alder cycloaddition reactions for straight-forward synthesis of endo-norbornene derivatives. Synlett, 2010. Vol. 19. P. 2895-2898.
[7] Dias L. Chiral Lewis acid catalysts in Diels-Alder cycloadditions aspects and synthetic applications of recent systems // J. Braz. Chem. Soc. 1997. Vol. 8, N 4. P. 289-332.
[8] McDaniel K., Weekly M. The Diels-Alder reaction of 2,4-hexadiene-1-ol with maleic anhydride // J. of Chemical Education. 1997. Vol. 74, N 12. P. 1464-1467.
[9] Gebauer M. Synthesis and Diels-Alder reactions of chiral 1,3-dienes: Dissert. candidate work. University of Adelaide, Australia, 1996. 139 p.
[10] Bozzo C., Mur N., Constans P. Furo[3.4-b]benzodioxin cycloadditions – a one pot synthesis of functionalized bis-adducts // J. of Organic Chemistry. 2009. P. 2174-2178.
[11] Dzyurkevich M., Krivolapov D., Lodochnikova Q. Synthesis and molecular structure of alloocimene adducts with maleic and citraconic anhydrides // Russian Journal of General Chemistry. 2011. Vol. 81, N 6. P. 1181-1184.
[12] Khafizova L.O., Yakupova L.R., Tuktarova R.A. Diels-Alder reactions of alumina- and magnesacyclopentadienes // Russian Journal of General Chemistry. 2008. Vol. 44, N 9. P. 13141317.
[13] Mamedov Je.G., Gasanov A.G., Ajubov I.G., Alieva S.T., Gurbanova M.M. Stereo- i jenantioselektivnyj sintez monoalkilovyh jefirov norbornendikarbonovoj kisloty i izuchenie ih biologicheskoj aktivnosti // Azerb. Him. Zhurnal. 2005. N 1. P. 77-80.
[14] Gasanov A.G., Mamedbejli Je.G., Ajubov I.G., Gusejnov N.S. Dieny S5 frakcii piroliza v termicheskih i kataliticheskih reakcijah (4+2)-cikloprisoedinenija // Neftehimija. 2013. Vol. 53, N 1. P. 58-61.