Mono-, Di-, and Trifluoroalkyl Substituent Effects on the Torquoselectivities of Cyclobutene and Oxetene Electrocyclic Ring Openings

Journal of Organic Chemistry

Volumn 80, Issue 23, 2015, Pages 11768-11772

  Honda, Kazuya ^a   Lopez, Steven A ^b   Houk, K N ^b   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENES;

CLOSED SHELLS; CYCLOBUTENE; ELECTROCYCLIC RINGS; FAVORABLE INTERACTIONS; ORBITAL INTERACTION; ORBITALS; SUBSTITUENT EFFECT; TRIFLUOROMETHYL;

DENSITY FUNCTIONAL THEORY;

CHEMICAL BINDING; DENSITY FUNCTIONAL THEORY; ORBIT; RING OPENING; ROTATION; SUBSTITUTION REACTION;

EID: 84948822848     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01361     Document Type: Article

References (29)

1. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395 10.1021/ja01080a054
2. Vogel, E. Angew. Chem. 1954, 66, 640 10.1002/ange.19540662008
3. Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989 10.1021/ja00337a067
4. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099 10.1021/ja00293a046
5. Jefford, C. W.; Bernardinelli, G.; Wang, Y.; Spellmeyer, D. C.; Buda, A.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1157 10.1021/ja00030a005
6. Lopez, S. A.; Houk, K. N. J. Org. Chem. 2014, 79, 6189-6195 10.1021/jo500919s
7. Walker, M.; Hietbrink, B. N.; Thomas, B. E., IV; Nakamura, K.; Kallel, E. A.; Houk, K. N. J. Org. Chem. 2001, 66, 6669 10.1021/jo010466f
8. Mangelinckx, S.; Van Speybroeck, V.; Vansteenkiste, P.; Waroquier, M.; De Kimpe, N. J. Org. Chem. 2008, 73, 5481 10.1021/jo800522b
9. Jaccob, M.; Jem, I. S.; Giri, S.; Venuvanalingam, P.; Chattaraj, P. K. J. Phys. Org. Chem. 2011, 24, 460 10.1002/poc.1785
10. Yu, H.; Chan, W.; Goddard, J. D. J. Am. Chem. Soc. 1990, 112, 7529 10.1021/ja00177a012
11. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2013.
12. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: New York, 2009.
13. Begue, J. P.; Delpon, D. B. Bioorganic and Medicinal Chemistry of Fluorine; Wiley-Blackwell: New York, 2008.
14. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432-2506 10.1021/cr4002879
15. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330 10.1039/B610213C
16. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319 10.1039/B711844A
17. He, Z.; Luo, T.; Hu, M.; Cao, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 3944-3947 10.1002/anie.201200140
18. Zine, K.; Petrignet, J.; Thibonnet, J.; Abarbri, M. Synlett 2012, 23, 755-759 10.1055/s-0031-1290596
19. Takeda, Y.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8659-8661 10.1002/anie.200703759
20. Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879-882 10.1002/anie.200353032
21. Aikawa, K.; Nakamura, Y.; Yokota, Y.; Toya, W.; Mikami, K. Chem.-Eur. J. 2015, 21, 96-100 10.1002/chem.201405677
22. Aikawa, K.; Hioki, Y.; Shimizu, N.; Mikami, K. J. Am. Chem. Soc. 2011, 133, 20092-20095 10.1021/ja2085299
23. Aikawa, K.; Shimizu, N.; Honda, K.; Hioki, Y.; Mikami, K. Chem. Sci. 2014, 5, 410-415 10.1039/C3SC52548A
24. Lee, P. S.; Zhang, X.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 5072-5079 10.1021/ja0287635
25. Niwayama, S.; Kallel, A. K.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813-2825 10.1021/jo950884i
26. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781-932 10.1002/anie.196907811
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision C.01; Gaussian Inc.: Wallingford, CT, 2010.
28. Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032 10.1063/1.474659
29. Bondi, A. J. Phys. Chem. 1964, 68, 441 10.1021/j100785a001