Synthesis of 5-alkyl-3,4-difluorofuran-2(5H)-ones by lactonisation. Effects of substituents on cyclisation ability of fluorinated 4-hydroxyalkanoates. DFT calculations of the cyclisation energies

Journal of Fluorine Chemistry

Volumn 162, Issue , 2014, Pages 45-59

  Hajduch, Jan ^a,b   Duda, Zdeněk ^a   Beran, Jiří ^a   Kvíčala, Jaroslav ^a   Paleta, Oldřich ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

5 Alkyl 3,4 difluorofuran 2(5H) ones; 5 Alkyl 3 fluorofuran 2(5H) ones; Dehydrofluorination; DFT lactonisation energy; Exo trig lactonisations; Methyl 2,3,3 trifluoroacrylate; Photo induced addition; Regioselective radical addition

Indexed keywords

EID: 84899542952     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.03.009     Document Type: Article

References (63)

1. S. Yamada, M. Noma, K. Hondo, T. Konno, and T. Ishihara J. Org. Chem. 73 2008 522 528
2. Y. Wang, and D.J. Burton J. Org. Chem. 71 2006 3859 3862
3. Y. Wang, and D.J. Burton J. Org. Chem. 70 2005 10743 10746
4. P.J. Crowley, J. Fawcett, B.M. Kariuki, A.C. Moralee, J.M. Percy, and V. Salafia Org. Lett. 4 2002 4125 4128
5. M. Essers, C. Mück-Lichtenfeld, and G. Haufe J. Org. Chem. 67 2002 4125 4128
6. J. Ichikawa, Y. Wada, M. Fujiwara, and K. Sakoda Synthesis 2012 2002 1917 1936
7. P. Chanteau, M. Essers, R. Plantler-Royon, G. Haufe, and R. Portella Tetrahedron Lett. 43 2002 1677 1680
8. L.U. Colmenares, X. Zou, J. Liu, A.E. Asato, and R.S.H. Liu J. Am. Chem. Soc. 121 1999 5803 5804
9. J. Kvíčala, J. Plocar, R. Vlasáková, O. Paleta, and A. Pelter Synlett 2012 1997 986 988
10. J. Kvíčala, R. Vlasáková, J. Plocar, O. Paleta, and A. Pelter Collect. Czech. Chem. Commun. 65 2000 772 788
11. O. Paleta, A. Pelter, and J. Kebrle Tetrahedron Lett. 35 1994 9259 9262
12. O. Paleta, A. Pelter, J. Kebrle, Z. Duda, and J. Hajduch Tetrahedron 56 2000 3197 3207
13. O. Paleta, Z. Duda, and A. Holý Mendeleev Commun. 2001 17 19
14. M. Schlosser, and D. Michel Tetrahedron 52 1996 99 108
15. B.E. Smart J. Fluorine Chem. 109 2001 3 11
16. K. Müller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
17. J.T. Welch, and S. Eswarakrishnan Fluorine in Bioorganic Chemistry 1991 Wiley Chichester
18. R.E. Banks, and K.C. Lowe Fluorine in Medicine in the 21st Century (Conference Papers) 1994 UMIST Manchester
19. A.J. Eliott R.E. Banks, B.E. Smart, J.C. Tatlow, Organofluorine Chemistry: Principles and Commercial Applications 1994 Plenum Press New York, NY
20. R. Filler, Y. Kobayashi, and L.M. Yagupolskii Organo-fluorine Compounds in Medicinal Chemistry and Biomedical Applications 1993 Elsevier Amsterdam
21. I. Ojima, J.R. McCarthy, and J.T. Welch Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 1996 American Chemical Society Washington, WA
22. V.A. Soloshonok Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets 1999 Wiley Chichester
23. G. Theodoridis A. Tressaud, Advances in Fluorine Science 2 2006 Elsevier Amsterdam 121 175
24. C. Isanbor, and D. OÍHagan J. Fluorine Chem. 127 2006 303 319
25. J.P. Bégué, D. Bonnet-Delpon, and Bioorganic Medicinal Chemistry of Fluorine 2008 Wiley Hoboken
26. A. Tressaud, and G. Haufe Fluorine and Health: Molecular Imaging Biomedical Materials and Pharmaceuticals 2008 Elsevier Amasterdam 553 778
27. S. Purser, P.R. Moore, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
28. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
29. B.E. Smart J. Fluorine Chem. 109 2001 3 11
30. D. O'Hagan J. Fluorine Chem. 131 2010 1071 1081
31. D. Desmaele Tetrahedron 48 1992 2925 2934 (references therein)
32. D.W. Knight Contemp. Org. Synth. 1 1994 287 315
33. A. Pelter, R.I.H. Al-Bayati, M.T. Ayoub, W. Lewis, P. Pardasani, and P. Hansel J. Chem. Soc., Perkin Trans 1 1987 717 742
34. P. Ge, and K.L. Kirk J. Fluorine Chem. 127 2006 1390 1397
35. P. Ge, and K.L. Kirk J. Org. Chem. 62 1997 3340 3343
36. V.P. Šendrik, O. Paleta, and V. Dědek Collect. Czech. Chem. Commun. 42 1977 2530 2536
37. J.D. LaZerte, and R.J. Koshar J. Am. Chem. Soc. 77 1955 910 914
38. Daikin Kogyo Co., Jpn Kokai Tokkyo Koho 8143 225 (1981) Chem. Abstr. 95 1981 186628
39. O. Paleta, V. Dědek, H. Rautchek, and H.-J. Timpe J. Fluorine Chem. 42 1989 345 353
40. R.N. Haszeldine, R. Rowland, R.P. Sheppard, and A.E. Tipping J. Fluorine Chem. 28 1985 291 302
41. O. Paleta, V. Dědek, S. Neuenfeld, and H.-J. Timpe Czech. Pat. 268 1989 247
42. C.L. Bumgardner, and J.P. Burgess Tetrahedron Lett. 33 1992 1683 1686
43. O. Paleta, J. Hajduch, and S. Bohm Tetrahedron Lett. 43 2002 481 485
44. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734 736
45. J.E. Baldwin, J. Cutting, W. Dupont, L.I. Kruse, R.C. Silberman, and Thomas Chem. Commun. 1976 736 738
46. J.E. Baldwin, R.C. Thomas, and L.I. Kruse J. Org. Chem. 42 1977 3846 3852
47. Y. Komatsu, F. Sasaki, S. Takei, and T. Kitazume J. Org. Chem. 63 1998 8058 8061
48. O. Paleta, A. Volkov, and J. Hetflejš J. Fluorine Chem. 102 2000 147 157
49. J. Yin, and T. Linker Tetrahedron 67 2011 2447 2461
50. J. Yin, and T. Linker Chem. Eur. J. 15 2009 49 52
51. Z. Crane, D. Goeddel, Y. Gan, and Y. Shi Tetrahedron 61 2005 6409 6417
52. T.P. Brady, S.H. Kim, K. Wen, C. Kim, and E.A. Theodorakis Chem. Eur. J. 11 2005 7175 7190
53. C. Kim, R. Hoang, and E.A. Theodorakis Org. Lett. 1 1999 1295 1297
54. J.H. Bushweller, and P.A. Bartlett J. Org. Chem. 54 1989 2404 2409
55. S.P. Breukelman, G.D. Meakins, and A.M. Roe J. Chem. Soc., Perkin Trans 1 1985 1627 1635
56. M.L. Bender Chem. Rev. 60 1960 53 113
57. S. Yamabe, T. Fukuda, and M. Ishii Theor. Chem. Acc. 130 2011 429 438
58. L. Reyes, I. Nicolás-Vázques, N. Mora-Diez, and J.R. Alvarez-Idaboy J. Org. Chem. 78 2013 2327 2335
59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.02 2009 Gaussian, Inc. Wallingford, CT
60. Y. Zhao, and D.G. Truhlar Theor. Chem. Acc. 120 2008 215 241
61. F. Weigend, and R. Ahlrichs Phys. Chem. Chem. Phys 7 2005 3297 3305
62. Semichem, Inc., R. Dennington II., T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, and R. Gilliland GaussView, Version 3.09 2003 Semichem, Inc. Shawnee Mission, KS
63. O. Paleta, and J. Koňárek Collect. Czech. Chem. Commun. 38 1973 66 73