A detailed study on thiocarbonyl ene reactions

Computational and Theoretical Chemistry

Volumn 1019, Issue 1, 2013, Pages 71-77

  Yuan, Liwei ^a   Hu, Qinzhi ^a   Yang, Qiwu ^a   Zhang, Wenqin ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

Concerted mechanism; DFT; Regioselectivity; Substituent effect; Thiocarbonyl ene reaction

Indexed keywords

EID: 84880990530     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2013.06.042     Document Type: Article

References (33)

1. Mikami K., Shimizu M. Asymmetric ene reactions in organic synthesis. Chem. Rev. 1992, 92:1021-1050.
2. Snider B.B. Lewis-acid-catalyzed ene reactions. Acc. Chem. Res. 1980, 13:426-432.
3. Dubac J., Laporterie A. Ene and retro-ene reactions in group 14 organometallic chemistry. Chem. Rev. 1987, 87:319-334.
4. Yôichi N., Kaoru K. A highly stereoselective preparation of l-isopulegol. Synthesis 1978, 147-148.
5. Okachi T., Fujimoto K., Onaka M. Practical carbonyl-ene reactions of methylstyrenes with paraformaldehyde promoted by a combined system of boron trifluoride and molecular sieves 4A. Org. Lett. 2002, 4:1667-1669.
6. Corma A., Renz M. Sn-Beta zeolite as diastereoselective water-resistant heterogeneous Lewis-acid catalyst for carbon-carbon bond formation in the intramolecular carbonyl-ene reaction. Chem. Commun. 2004, 550-551.
7. Xia Q., Ganem B. Asymmetric total synthesis of (-)-α-kainic acid using an enantioselective, metal-promoted ene cyclization. Org. Lett. 2001, 3:485-487.
8. Choi S.S.M., Kirby G.W., Mahajan M.P. J. Chem. Soc., Chem. Commun. 1990, 138-140.
9. Heus-Kloos Y.A., De Jong R.L.P., Verkruijsse H.D., Brandsma L., Julia S. A facile synthesis of 1,1-bis[methylthio]-1,3-alksdienes. Synthesis 1985, 1985:958-959.
10. Middleton W.J. Fluorothiocarbonyl compounds. IV. Hexafluorothioacetone-olefin adducts. J. Org. Chem. 1965, 30:1395-1398.
11. Kirby G.W., McGregor W.M. The transient dienophile diethyl thioxomalonate and its S-Oxide (sulphine) formed by retro-Diels-Alder cleavage reactions. J. Chem. Soc., Perkin Trans. 1 1990, 3175-3181.
12. Bladon C.M., Ferguson I.E.G., Kirby G.W., Lochead A.W., McDougall D.C. Ethyl and methyl thioxoacetates, dienophilic thioaldehydes formed from sulphenyl chlorides by 1,2-elimination. J. Chem. Soc., Perkin Trans. 1 1985, 1541-1545.
13. Bachrach S.M., Jiang S. Ab initio study of the thio-ene reaction. 1. The enophile substituent effect. J. Org. Chem. 1997, 62:8319-8324.
14. Fernández I., Bickelhaupt F.M. Alder-ene reaction: aromaticity and activation-strain analysis. J. Comput. Chem. 2012, 33:509-516.
15. Yang Q., Tong X., Zhang W. Influence of Lewis acids and substituents on carbonyl-ene reactions: a density functional theory study. J. Mol. Struct. THEOCHEM 2010, 957:84-89.
16. Yang Q., Liu Y., Zhang W. A theoretical study of imine-ene reaction influencing factors. Org. Biomol. Chem. 2011, 9:6343-6351.
17. Loncharich R.J., Houk K.N. Transition structures of ene reactions of ethylene and formaldehyde with propene. J. Am. Chem. Soc. 1987, 109:6947-6952.
18. Paderes G.D., Jorgensen W.L. Computer-assisted mechanistic evaluation of organic reactions. 20. Ene and retro-ene chemistry. J. Org. Chem. 1992, 57:1904-1916.
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, J. T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople. Gaussian 03, revision B.05 Gaussian, Inc. Pittsburgh, PA, 2003.
20. Lee C., Yang W., Parr R.G. Development of the Colic-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B. 1988, 37:785-789.
21. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
22. Fukui K. A formulation of the reaction coordinate. J. Chem. Phys. 1970, 74:4161-4163.
23. Ishida K.A.K., Morokuma K., Komornicki A. The intrinsic reaction coordinate. An ab initio calculation for HNC→HCN and H-+CH4-→CH4+H-. J. Chem. Phys. 1977, 66:2153-2156.
24. Reed A.E., Weinstock R.B., Weinhold F. Natural population analysis. J. Chem. Phys. 1985, 83:735-746.
25. Reed A.E., Curtiss L.A., Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88:899-926.
26. Biegler-König F., Schönbohm J., Bayles D. Software news and updates AIM2000 - a program to analyze and visualize atoms in molecules. J. Comput. Chem. 2001, 22:545-559.
27. F. Biegler-König, J. Schönbohm, AIM2000 2.0., 2002.
28. Parr R.G., Szentpály L.v., Liu S. Electrophilicity index. J. Am. Chem. Soc. 1999, 121:1922-1924.
29. Parr R.G., Pearson R.G. Absolute dardness: companion parameter to absolute electronegativity. J. Am. Chem. Soc. 1983, 105:7512-7516.
30. Domingo L.R., Chamorro E., Pérez P. Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study. J. Org. Chem. 2008, 12:4615-4624.
31. Domingo L.R., Sáez J.A. The nucleophilicity N index in organic chemistry. Org. Biomol. Chem. 2011, 9:7168-7175.
32. Domingo L.R., Pérez P. Understanding the mechanism of polar Diels-Alder reactions. Org. Biomol. Chem. 2009, 7:3576-3583.
33. Domingo L.R., Aurell M.J., Pérez P., Contreras R. Quantitanative characterization of the global electrophilicity power od common diene/dienophile pair in Diels-Alder reactions. Tetrahedron 2002, 58:4417-4423.