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34
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78650918240
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Both commercially available sodium p -toluenesulfinate and sodium p -toluenesulfinate hydrate could be employed with equal success.
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Both commercially available sodium p -toluenesulfinate and sodium p -toluenesulfinate hydrate could be employed with equal success.
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-
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-
35
-
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78650853580
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DMAc was found to be the superior solvent for this reaction; nonpolar aprotic solvents resulted in no reaction.
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DMAc was found to be the superior solvent for this reaction; nonpolar aprotic solvents resulted in no reaction.
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-
-
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36
-
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65949119347
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For a related transformation on a chloropyridine in the absence of TBACl, see
-
For a related transformation on a chloropyridine in the absence of TBACl, see: Caron, S.; Do, N. M.; Sieser, J. E.; Whritenour, D. C.; Hill, P. D. Org. Process Res. Dev 2009, 13, 324
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Caron, S.1
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Whritenour, D.C.4
Hill, P.D.5
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38
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78650868394
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The solubility of sodium p -toluenesulfinate in DMAC at rt was measured to be 1.0 mg/mL and at 100 °C was 1.5 mg/mL by HPLC analysis.
-
The solubility of sodium p -toluenesulfinate in DMAC at rt was measured to be 1.0 mg/mL and at 100 °C was 1.5 mg/mL by HPLC analysis.
-
-
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39
-
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78650863250
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2Tol was completely soluble in DMAc at 100 °C.
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2Tol was completely soluble in DMAc at 100 °C.
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-
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40
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78650877898
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While protonation of sodium p -toluenesulfinate is a possibility in the presence of HCl, the fact that these reactions proceed to completion and in high yield suggest that protonation of the pyridine nitrogen is faster.
-
While protonation of sodium p -toluenesulfinate is a possibility in the presence of HCl, the fact that these reactions proceed to completion and in high yield suggest that protonation of the pyridine nitrogen is faster.
-
-
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41
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78650892975
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3-Bromopyridine, 3-fluoropyridine, and 3-iodopyridine also failed to react with sulfinate 2.
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3-Bromopyridine, 3-fluoropyridine, and 3-iodopyridine also failed to react with sulfinate 2.
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-
-
-
42
-
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78650856127
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For the preparation of compound 26 under similar conditions, see
-
For the preparation of compound 26 under similar conditions, see
-
-
-
-
44
-
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1842868807
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Freeman, F.; Bartosik, L. G.; Van Bui, N.; Keindl, M. C.; Nelson, E. L. Phosphorus Sulfur 1988, 53, 375
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Freeman, F.1
Bartosik, L.G.2
Van Bui, N.3
Keindl, M.C.4
Nelson, E.L.5
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45
-
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78650916687
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-
Although not investigated in the present study, the methodology should be applicable to other types of alkyl and aryl sulfinate salts.
-
Although not investigated in the present study, the methodology should be applicable to other types of alkyl and aryl sulfinate salts.
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