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79953904243
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3- d) = 0.6 ppm) confirms the absence of the intramolecular hydrogen bond in solutions. A relative energy of (P) and (M) atropisomers of (Z)- 4e was calculated by using the B3LYP/6-31G(d,p) basis set (see the Supporting Information for details).
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0001304511
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3 = 333 K). The Gibbs free energy of activation at T = 298 K was calculated from the Eyring plot of the atropisomerization rate constants vs inverse temperature (see the Supporting Information, pp S3-S4, for details)
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A 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: 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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(1996)
J. Chem. Soc., Perkin Trans. 1
, pp. 691
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Hose, D.R.J.1
Mahon, M.F.2
Molloy, K.C.3
Raynham, T.4
Wills, M.5
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68
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28844485734
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Chelucci, G.; Baldino, S.; Chessa, S. Tetrahedron 2006, 62, 619
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(2006)
Tetrahedron
, vol.62
, pp. 619
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Chelucci, G.1
Baldino, S.2
Chessa, S.3
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69
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0033993072
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Atomic charge calculations have demonstrated considerable negative charge on oxygen in sulfinylimines
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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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(2000)
Chem. Soc., Perkin Trans. 2
, pp. 43
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Bharatam, P.V.1
Uppal, P.2
Kaur, D.J.3
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70
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79953855045
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3ÂTHF at -78 °C (Conditions A: Table 3, entries 11 and 14)
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3ÂTHF at -78 °C (Conditions A: Table 3, entries 11 and 14).
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71
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79953852542
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8, 3 h) as evidenced by NMR (see the Supporting Information, p S7, for details)
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8, 3 h) as evidenced by NMR (see the Supporting Information, p S7, for details).
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72
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79953871302
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The atropisomerization barrier of 97.9 kJ/mol at 25 °C (see Table 2) corresponds to an isomerization half-life (conversion of a pure atropisomer (Z)-(P)- 4f to a (P):(M)=75:25 mixture) of 4.3 h. In fact, the actual (P)(M) isomerization rate is higher because the backward (M)(P) transformation is suppressed due to the rapid reduction of the more reactive atropisomer (Z)-(M)- 4f immediate upon forming
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The atropisomerization barrier of 97.9 kJ/mol at 25 °C (see Table 2) corresponds to an isomerization half-life (conversion of a pure atropisomer (Z)-(P)- 4f to a (P):(M)=75:25 mixture) of 4.3 h. In fact, the actual (P)(M) isomerization rate is higher because the backward (M)(P) transformation is suppressed due to the rapid reduction of the more reactive atropisomer (Z)-(M)- 4f immediate upon forming.
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73
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79953906489
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8 solution under the reduction conditions
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8 solution under the reduction conditions.
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74
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79953898981
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S, S)- 7d was confirmed by X-ray analysis (see the Supporting Information)
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S, S)- 7d was confirmed by X-ray analysis (see the Supporting Information).
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75
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0346362496
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Prepared following the procedure described in the literature
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Prepared following the procedure described in the literature: Nguyen, P.; Corpuz, E.; Heidelbaugh, T. M.; Chow, K.; Garst, M. E. J. Org. Chem. 2003, 68, 10195
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(2003)
J. Org. Chem.
, vol.68
, pp. 10195
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Nguyen, P.1
Corpuz, E.2
Heidelbaugh, T.M.3
Chow, K.4
Garst, M.E.5
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76
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15644370082
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Prepared as described by
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Prepared as described by: Pierce, M. E.; Parsons, R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 8536
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(1998)
J. Org. Chem.
, vol.63
, pp. 8536
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Pierce, M.E.1
Parsons Jr., R.L.2
Radesca, L.A.3
Lo, Y.S.4
Silverman, S.5
Moore, J.R.6
Islam, Q.7
Choudhury, A.8
Fortunak, J.M.D.9
Nguyen, D.10
Luo, C.11
Morgan, S.J.12
Davis, W.P.13
Confalone, P.N.14
Chen, C.15
Tillyer, R.D.16
Frey, L.17
Tan, L.18
Xu, F.19
Zhao, D.20
Thompson, A.S.21
Corley, E.G.22
Grabowski, E.J.J.23
Reamer, R.24
Reider, P.J.25
more..
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77
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79953901647
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To avoid isomerization of individual atropisomers in eluate, collected fractions were cooled to -78 °C (dry ice-acetone bath)
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To avoid isomerization of individual atropisomers in eluate, collected fractions were cooled to -78 °C (dry ice-acetone bath).
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78
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0343458589
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Wiley: New York,; Vol., pp - 595
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Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; Wiley: New York, 1967; Vol. 1, pp 581 - 595.
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(1967)
Reagents for Organic Synthesis
, vol.1
, pp. 581
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Fieser, L.F.1
Fieser, M.2
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