Previous_Amine_Reactions_2009 - 2 group to amine R NHR' O...

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1 Amines and Their Reactions Encountered in Previous Chapters R NH 2 O R N OH H R N OH OH R NH 2 CN R N CN H alkylation by conjugate addition alkylation by epoxide ring opening 2 O RNH 2 NaBH 3 CN AcOH N H R Reductive amination O R 2 NH NaBH(OOCCH 3 ) 3 AcOH N R R Reductive amination O AcOH N R R NaBH(OOCCH 3 ) 3 AcOH N R R Reductive amination R 2 NH O RNH 2 H + catalyst N R EtOH N H R Reductive amination NH 2 NaNO 2 HCl or HNO 2 nitrous acid N 2 + Cl Diazotization to form a diazonium salt N 2 + Cl H 2 O OH — N 2 + HCl H 2 , Pt N 2 + Cl X Sandmeyer Reaction: X = Cl, Br, I, CN) CuX
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2 NH O O N O O R—X (X = Br, I, OTs) N—R O O 1. H 3 O + 2. HO COO COO Gabriel Synthesis of primary amines NO 2 Sn/HCl or Fe/HCl or H 2 , Pd/C NH 2 Reduction of NO
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Unformatted text preview: 2 group to amine R NHR' O 1. LiAlH 4 2. H 3 O + R NHR' Reduction of amides KH or KOH R Br R CN R Reduction of nitriles to form primary amines 2. H 2 O NH 2 O H H O O NHR Mannich Reaction 1. LiAlH 4 ! RNH 2 K + RNH 2 NaCN Related to reductive amination but with no reducing agent Other concepts to review 1. Simple nomenclature 2. Basicity factors affecting basicity, aromaticity, aliphatic vs aromatic amines, substituent effect, resonance, inductive effects...
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This note was uploaded on 05/13/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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Previous_Amine_Reactions_2009 - 2 group to amine R NHR' O...

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