The first example of the configurational assignment at the C=N bond of allenylthioimidates

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7367-7371

  Krivdin, Leonid B ^a   Nedolya, Nina A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

Allenylthioimidates; Carbon carbon spin spin coupling constants; Conformational analysis; DFT B3LYP; E Z Isomers; NMR; SOPPA

Indexed keywords

ALLENE DERIVATIVE; IMIDE;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; LOW TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 25444524859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.118     Document Type: Article

References (61)

1. L. Brandsma, and H. Verkruijsse Preparative Polar Organometallic Chemistry Vol. 1 1987 Springer Berlin, Heidelberg, N.Y., London, Paris, Tokyo 240p
2. L. Brandsma Best Synthetic Methods; Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques 2004 Elsevier, Academic Press Amsterdam, Boston, Heidelberg, London, N.Y., Oxford, Paris, San Diego, San Francisco, Sydney, Tokyo 469p
3. Nedolya, N. A. Novel Chemistry Based on Isothiocyanates and Polar Organometallics. Ph.D. Thesis, Utrecht University, The Netherlands; 1999, 144p.
4. For recent reviews, see: L. Brandsma, N.A. Nedolya, O.A. Tarasova, and B.A. Trofimov Chem. Heterocycl. Compd. (N.Y.) 36 2000 1241 1260
5. L. Brandsma Eur. J. Org. Chem. 2001 4569 4581
6. L. Brandsma, and N.A. Nedolya Synthesis 2004 735 745
7. O.A. Tarasova, N.A. Nedolya, L. Brandsma, and A.I. Albanov Tetrahedron Lett. 45 2004 5881 5883
8. N.A. Nedolya, L. Brandsma, and B.A. Trofimov Khim. Geterotsikl. Soedin. 1996 917 918
9. N.A. Nedolya, R.-J. de Lang, L. Brandsma, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 33 1997 76 79
10. N.A. Nedolya, L. Brandsma, V.P. Zinov'eva, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 33 1997 80 85
11. L. Brandsma, N.A. Nedolya, O.A. Tarasova, L.V. Klyba, L.M. Sinegovskaya, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 35 1999 928 932
12. N.A. Nedolya, and L. Brandsma Russ. J. Org. Chem. 39 2003 609 610
13. L. Brandsma, N.A. Nedolya, R.-J. de Lang, and B.A. Trofimov Russ. Chem. Bull. (Engl. Transl.). 45 1996 2873 2874
14. F. Taherirastgar, N.A. Nedolya, L. Brandsma, R.-J. de Lang, and B.A. Trofimov Dokl. Chem. (Engl. Transl.). 353 1997 39 40
15. L. Brandsma, N.A. Nedolya, R.-J. de Lang, and B.A. Trofimov Chem. Heterocycl. Compd. (N.Y.). (Engl. Transl.). 33 1997 491 492
16. N.A. Nedolya, L. Brandsma, R.-J. de Lang, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 33 1997 1361 1362
17. L. Brandsma, N.A. Nedolya, H.D. Verkruijsse, N.L. Owen, Du Li, and B.A. Trofimov Tetrahedron Lett. 38 1997 6905 6908
18. N.A. Nedolya, L. Brandsma, and B.A. Trofimov Russ. Chem. Bull. (Engl. Transl.). 45 1996 2670 2671
19. N.A. Nedolya, L. Brandsma, and B.A. Trofimov Dokl. Chem. (Engl. Transl.). 350 1996 210 211
20. N.A. Nedolya, L. Brandsma, V.P. Zinov'eva, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 34 1998 1494 1499
21. N.A. Nedolya, L. Brandsma, R.-J. de Lang, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 33 1997 580 581
22. N.A. Nedolya, N.I. Schlyakhtina, L.V. Klyba, I.A. Ushakov, S.V. Fedorov, and L. Brandsma Tetrahedron Lett. 43 2002 9679 9681
23. N.A. Nedolya, L. Brandsma, and B.A. Trofimov Khim. Geterotsikl. Soedin. 2002 1396 1398
24. L. Brandsma, N.A. Nedolya, A.C.H.T.M. van der Kerk, V. Heerma, E.T.H.G. Lutz, R.-J. de Lang, A.V. Afonin, and B.A. Trofimov Russ. Chem. Bull. (Engl. Transl.). 46 1997 832 833
25. L. Brandsma, N.A. Nedolya, V. Heerma, A.C.H.T.M. van der Kerk, E.T.H.G. Lutz, R.-J. de Lang, A.V. Afonin, and B.A. Trofimov Chem. Heterocycl. Compd. (N.Y.). (Engl. Transl.). 33 1997 493 495
26. N.A. Nedolya, L. Brandsma, A.C.H.T.M. van der Kerk, V. Heerma, E.T.H.G. Lutz, A.V. Afonin, R.-J. de Lang, and B.A. Trofimov Russ. J. Org. Chem. (Engl. Transl.). 33 1997 1359 1360
27. N.A. Nedolya, L. Brandsma, O.A. Tarasova, H.D. Verkruijsse, and B.A. Trofimov Tetrahedron Lett. 39 1998 2409 2410
28. V.A. Shagun, D.-S.D. Toryashinova, N.A. Nedolya, O.A. Tarasova, and L. Brandsma Russ. J. Org. Chem. 40 2004 775 789
29. L. Brandsma, N.A. Nedolya, and B.A. Trofimov Eur. J. Org. Chem. 1999 2663 2664
30. L.B. Krivdin, G.A. Kalabin, R.N. Nesterenko, and B.A. Trofimov Tetrahedron Lett. 25 1984 4817 4820
31. G.A. Kalabin, L.B. Krivdin, V.V. Shcherbakov, and B.A. Trofimov J. Mol. Struct. 143 1986 569 572
32. L.B. Krivdin, V.V. Shcherbakov, and G.A. Kalabin Russ. J. Org. Chem. (Engl. Transl.) 22 1986 300 305
33. L.B. Krivdin, N.A. Scherbina, and N.V. Istomina Magn. Reson. Chem. 43 2005 435 443
34. V. Barone, J.E. Peralta, R.H. Contreras, A.V. Sosnin, and L.B. Krivdin Magn. Reson. Chem. 39 2001 600 606
35. L.B. Krivdin, S.V. Zinchenko, V.V. Shcherbakov, G.A. Kalabin, R.H. Contreras, M.F. Tufro, M.C. Ruiz de Azua, and C.G. Giribet J. Magn. Reson. 84 1989 1 8
36. R.H. Contreras, C.G. Giribet, M.C. Ruiz de Azua, C.N. Cavasotto, and L.B. Krivdin J. Mol. Struct. (Theochem) 210 1990 175 186
37. L.B. Krivdin, S.V. Zinchenko, G.A. Kalabin, M.F. Tufro, R.H. Contreras, A.Yu. Denisov, O.A. Gavrilyuk, and V.I. Mamatyuk J. Chem. Soc., Faraday Trans. 88 1992 2459 2463
38. E.S. Nielsen, P. Jørgensen, and J. Oddershede J. Chem. Phys. 73 1980 6238 6246
39. M.J. Packer, E.K. Dalskov, T. Enevoldsen, H.J.A. Jensen, and J. Oddershede J. Chem. Phys. 105 1996 5886 5900
40. T. Enevoldsen, J. Oddershede, and S.P.A. Sauer Theor. Chem. Acc. 100 1998 275 284
41. K.L. Bak, H. Koch, J. Oddershede, O. Christiansen, and S.P.A. Sauer J. Chem. Phys. 112 2000 4173 4185
42. L.B. Krivdin, S.P.A. Sauer, J.E. Peralta, and R.H. Contreras Magn. Reson. Chem. 40 2002 187 194
43. L.B. Krivdin Magn. Reson. Chem. 41 2003 91 101
44. L.B. Krivdin Magn. Reson. Chem. 41 2003 157 168
45. L.B. Krivdin Magn. Reson. Chem. 41 2003 417 430
46. L.B. Krivdin Magn. Reson. Chem. 41 2003 885 901
47. L.B. Krivdin Magn. Reson. Chem. 42 2004 1 13
48. L.B. Krivdin Magn. Reson. Chem. 42 2004 500 511
49. S.P.A. Sauer, and L.B. Krivdin Magn. Reson. Chem. 42 2004 671 686
50. L.B. Krivdin Magn. Reson. Chem. 42 2004 S168 S179
51. L.B. Krivdin Magn. Reson. Chem. 42 2004 919 930
52. L.B. Krivdin Magn. Reson. Chem. 43 2005 101 116
53. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S.J. Su, T.L. Windus, M. Dupuis, and J.A. Montgomery J. Comp. Chem. 14 1993 1347 1363
54. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
55. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B. 37 1988 785 789
56. R. Krisnan, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650 654
57. Agren, H.; Angeli, C.; Bak, K. L.; Bakken, V.; Christiansen, O.; Cimiraglia, R.; Coriani, S.; Dahle, P.; Dalskov, E. K.; Enevoldsen, T.; Fernandez, B.; Haettig, C.; Hald, K.; Halkier, A.; Heiberg, H.; Helgaker, T.; Hettema, H.; Jensen, H. J. A.; Jonsson, D.; Joergensen, P.; Kirpekar, S.; Klopper, W.; Kobayashi, R.; Koch, H.; Ligabue, A.; Lutnaes, O. B.; Mikkelsen, K. V.; Norman, P.; Olsen, J.; Packer, M. J.; Pedersen, T. B.; Rinkevicius, Z.; Rudberg, E.; Ruden, T. A.; Ruud, K.; Salek, P.; Sanchez de Meras, A.; Saue, T.; Sauer, S. P. A.; Schimmelpfennig, B.; Sylvester-Hvid, K. O.; Taylor, P. R.; Vahtras, O.; Wilson, D. J. Dalton, A Molecular Electronic Structure Program, Release 2.0, 2005, see, http://www.kjemi.uio.no/software/dalton/dalton.html.
58. T.H. Dunning Jr. J. Chem. Phys. 90 1989 1007 1023
59. R.A. Kendall, T.H. Dunning Jr., and R.J. Harrison J. Chem. Phys. 96 1992 6796 6806
60. D.E. Woon, and T.H. Dunning Jr. J. Chem. Phys. 98 1993 1358 1371
61. D.E. Woon, and T.H. Dunning Jr. J. Chem. Phys. 103 1995 4572 4585