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17.10 Reaction with Primary Amines: Imines

17.10 Reaction with Primary Amines: Imines. Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage. Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction.

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17.10 Reaction with Primary Amines: Imines

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  1. 17.10Reaction with Primary Amines:Imines

  2. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  3. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  4. H2N R Imine (Schiff's Base) Formation •• •• + H HN C O C O •• •• •• •• R a carbinolamine •• N + H2O C (imine) R

  5. O CH Example + CH3NH2 CH=NCH3 + H2O N-Benzylidenemethylamine (70%)

  6. O CH Example + CH3NH2 OH CH NHCH3 CH=NCH3 + H2O N-Benzylidenemethylamine (70%)

  7. Example + (CH3)2CHCH2NH2 O NCH2CH(CH3)2 + H2O N-Cyclohexylideneisobutylamine (79%)

  8. Example + (CH3)2CHCH2NH2 O OH NHCH2CH(CH3)2 NCH2CH(CH3)2 + H2O N-Cyclohexylideneisobutylamine (79%)

  9. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  10. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  11. + NG + R2C H2O H2N G O R2C Reaction with Derivatives of Ammonia

  12. + NG + R2C H2O H2N G O R2C NOH R2C H2N OH Reaction with Derivatives of Ammonia hydroxylamine oxime

  13. O CH3(CH2)5CH + H2NOH NOH CH3(CH2)5CH + H2O Example (81-93%)

  14. + NG + R2C H2O H2N G O R2C NOH R2C H2N OH NNH2 R2C H2N NH2 Reaction with Derivatives of Ammonia hydroxylamine oxime hydrazine hydrazone etc.

  15. O C NNH2 C Example + H2NNH2 + H2O (73%)

  16. O NNH CCH3 Example CCH3 + H2NNH phenylhydrazine + H2O a phenylhydrazone (87-91%)

  17. O O H2NNHCNH2 O NNHCNH2 CH3(CH2)9CCH3 Example + CH3(CH2)9CCH3 semicarbazide + H2O a semicarbazone (93%)

  18. 17.11Reaction with Secondary Amines:Enamines

  19. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  20. Some reactions of aldehydes and ketones progressbeyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

  21. C H C H •• •• •• C O H R2N R2NH O C •• •• •• C •• C R2N Enamine Formation +H2O (enamine)

  22. O Example (heat in benzene) N + NH (80-90%)

  23. O N OH Example (heat in benzene) N + NH via

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