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(a) Afarinkia, K.; Rees, C. W.; Cadogan, J. I. G. Tetrahedron 1990, 46, 7175.
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35348953795
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The silylated diethyl phosphite was prepared in a separate reaction. Triethylammonium salts were removed from the reagent
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(b) The silylated diethyl phosphite was prepared in a separate reaction. Triethylammonium salts were removed from the reagent.
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35348954306
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31P coupling).
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31P coupling).
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35348977196
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2-MeOH (81:17:3).
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2-MeOH (81:17:3).
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35348975085
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Detailed Description of the Procedure In an oven-dry flask, hydrazone 2 (2 mmol) is dissolved in abs. EtOH. To this solution, triethyl phosphite (10 mmol, 5 equiv) is added. This mixture is brought to reflux temperature under an N2 atmosphere and formic acid (5 equiv) is added by a syringe. The reaction is followed with 31P NMR. When no changes are observed anymore (after several days) the reaction is stopped. The solvent is evaporated and the residue redissolved in Et2O (20 mL, After pouring into 3 N HCl (30 mL) this system is extracted 3 times with Et 2O (20 mL, The aqueous phase is made basic with 3 N NaOH and extracted three times with CH2Cl2 (20 mL, The combined organic layers are dried over MgSO4. After filtration, the solvent is evaporated in vacuo. 1H NMR, 13C NMR, IR, and MS spectra were entirely consistent with the assigned structures. Selected example:
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