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Amines (McM chapt 24)

Amines (McM chapt 24). pKa Alkylamines: ca 9-11 Arylamines: ca 4-5 (anilines). Synthesis (McM 24.6). From KJ101 / KJM1010+1020:. Alkylation (ammonia or amine, phtalimide). Reductive amination. Reductions. Synthesis (McM 24.6): “New” reactions. Hofmann rearrangement.

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Amines (McM chapt 24)

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  1. Amines (McM chapt 24) pKa Alkylamines: ca 9-11 Arylamines: ca 4-5 (anilines)

  2. Synthesis (McM 24.6) From KJ101 / KJM1010+1020: Alkylation (ammonia or amine, phtalimide) Reductive amination

  3. Reductions

  4. Synthesis (McM 24.6): “New” reactions Hofmann rearrangement

  5. Curtius rearrangement

  6. Reactions of amines (Alkylamines) (McM 24.7) • Alkylamines: • Alkylation (McM 24.7) • Acylation (McM 21.4, 21.5) • Hofmann elimination (≠ Hofmann rearrangement) E2 elimination to form alkene X= halogen, (OH) X ≠ NR2 Strong base / bad leaving group

  7. Removal of less sterically hindered H Not necessarily most stable alkene formed Morphine Codeine

  8. Reactions of Arylamines (aniline derivatives) (McM 24.8) • Weak base (pKa ca 4.6) • Highly Activated for E-fil Ar Subst (o/p) • Protect. as amide: Less activated, still o/p Nucleophilic Aromatic Substitution - Mechanisms • SNAr √ • SN1 • Benzyne √ • SRN1: Involves radicals • (VNS: Vicarious Nucl. Subst.)

  9. Formation of Diazonium Salts and the Sandmeyer Reaction N2 as leaving group Cu-salt mediated react. Sandmeyer react. (radical mech.)

  10. Diazo coupling Antibacterial sulfonamides

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