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77950310212
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Supporting Information
-
For preparation of ketones 3a-h, see Supporting Information, pages S2-S10.
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43
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31544442292
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77950335134
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Stabilization of the E-isomer in β by the intramolecular hydrogen bond between the β-hydroxy group and the oxygen of sulfinyl imine has been suggested; see ref 8c.
-
Stabilization of the E-isomer in β by the intramolecular hydrogen bond between the β-hydroxy group and the oxygen of sulfinyl imine has been suggested; see ref 8c.
-
-
-
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45
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28844485734
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See for example: Chelucci, G.; Baldino, S.; Chessa, S. Tetrahedron 2006, 62, 619.
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Chelucci, G.1
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0040387312
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For the influence of solvent on ratio of isomers, see: Stassinopoulou, C. I.; Zioudrou, C.; Karabatsos, G. J. Tetrahedron 1976, 32, 1147.
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-
-
77950331033
-
-
3-d at -15 °C, the amount of major diastereomer of 4a was 96.8%.
-
3-d at -15 °C, the amount of major diastereomer of 4a was 96.8%.
-
-
-
-
49
-
-
77950306813
-
-
1H HMBC experiments.
-
1H HMBC experiments.
-
-
-
-
50
-
-
77950328903
-
-
A protons in Z-isomers were constantly shifted downfield Δδ =
-
A by the phenyl ring. See the Supporting Information (Table S1, page S11) for details.
-
-
-
-
51
-
-
77950321213
-
-
Related diaryl sulfinylketimines were obtained as a rapidly interconverting mixtures of Z- and E-isomers; see ref 8b.
-
Related diaryl sulfinylketimines were obtained as a rapidly interconverting mixtures of Z- and E-isomers; see ref 8b.
-
-
-
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54
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0001869332
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(c) Abel, E. W.; Coston, T. P. J.; Orrell, K. G.; Sik, V.; Stephenson, D. J. Magn. Reson. 1986, 70, 34.
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56
-
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37049093376
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3-d has been determined for structurally related p-toluenesulfinylketimines. (a) Di-(p-tolyl)methylenep- toluenesulfinamide, 15 kcal/mol (62.8 kJ/mol)
-
3-d has been determined for structurally related p-toluenesulfinylketimines. (a) Di-(p-tolyl)methylenep- toluenesulfinamide, 15 kcal/mol (62.8 kJ/mol): Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. 11982, 339.
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Annunziata, R.1
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57
-
-
33847799061
-
-
Diphenylmethylene benzenesulfinamide, 14.1 kcal/mol (59.0 kJ/mol)
-
(b) Diphenylmethylene benzenesulfinamide, 14.1 kcal/mol (59.0 kJ/mol): Davis, F. A.; Kluger, E. W. J. Am. Chem. Soc. 1976, 98, 302.
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Davis, F.A.1
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58
-
-
77950312730
-
-
c = 2.22Δv and the Eyring equation(k = 1); see ref 20b.
-
c = 2.22Δv and the Eyring equation(k = 1); see ref 20b.
-
-
-
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59
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0033543624
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-
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77950334381
-
-
8 at -15 °C (see Table 3).
-
8 at -15 °C (see Table 3).
-
-
-
-
62
-
-
0001019841
-
-
Cyclic six-membered transition state has been proposed in the reduction of sulfinylketimines with DIBAL: (a)
-
Cyclic six-membered transition state has been proposed in the reduction of sulfinylketimines with DIBAL: (a) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691.
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63
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77950307600
-
-
Ref 12.
-
(b) Ref 12.
-
-
-
-
64
-
-
0033993072
-
-
Atomic charge calculations have demonstrated considerable negative charge on oxygen in sulfinylimines
-
Atomic charge calculations have demonstrated considerable negative charge on oxygen in sulfinylimines: Bharatam, P. V.; Uppal, P.; Kaur, D. J. Chem. Soc., Perkin Trans. 2 2000, 43.
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Bharatam, P.V.1
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65
-
-
77950308362
-
-
note
-
3 or DIBAL to the anion to afford an amidometallohydride prior to the H transfer is conceivable. The observed correlation with E/Z ratio of starting (E)-4a suggests an increased barrier for E/Z interconversion for the anion, which slows down the rate of equilibration on the reduction time scale.
-
-
-
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67
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0000286254
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(b) Jensen, J. A.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1988, 110, 4977.
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Jensen, J.A.1
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68
-
-
77950334190
-
-
4 (ref 20a).
-
4 (ref 20a).
-
-
-
-
69
-
-
77950329486
-
-
4 (reft 8g and 8i)
-
4 (reft 8g and 8i).
-
-
-
-
70
-
-
0032547296
-
-
Synthesized according to the reported procedure: Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
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Cogan, D.A.1
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Ellman, J.A.5
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