Reagents and-their-important-roles-in-the-functional-group-interconcersions


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Reagents and-their-important-roles-in-the-functional-group-interconcersions

  1. 1. Grc`s Collection in Organic synthesis 1
  2. 2. Grc`s Collection in Organic synthesis 2 Chromium reagents:Cr (IV) reagents H2CrO4,HCrO-4,CrO4-2,HCr2O7,Cr2O7-2,H2Cr2O7 and H2Cr2O7- …Oxidation of alcohol accompanied by reduction of the Cr(VI) to Cr(III).. CrO3 in H2O or Aq AcOH: CrO3 in acetone with H2SO4(Jones reagent): CrO3-Pyridine(Sarett oxidation): CrO3-Pyridine-DCM(Collins reagent): Pyridinium chloro chromate(Corey`s reagent):
  3. 3. Grc`s Collection in Organic synthesis 3 Pyridinium dichromate: 10 Alcohols to 20 Aldehydes:DMSO,Collins, coreys,PDC,Pr4N+RuO4-,CAN,Na2Cr2O7 in H2O,Hg2CO3-Celite, Hot HNO3 in Aq Glyme,Cr2Pyridine-CuCl,LTA-pyridine,Benzoyl peroxide-NiBr2.. DMSO(Di methyl sulfoxide): O S O Moffats(DMSO+DCC(dicyclo hexyl carbidoimide)+acid): OSiPh2tBu OSiPh2tBu MeO O MeO O OH O Dess martin periodinane oxidation: Ley Oxidation(tetra propyl ammonium per ruthinate): Oppenauer oxidation(Acetone/Al(O i-Pr)3): MPV reduction(meerwein pondarf vierly ): MnO2: It oxidizes only allylic &benzylic alcohols to their respective carbonyl compounds,
  4. 4. Grc`s Collection in Organic synthesis 4 Fetizon`s reagent(Ag2CO3 on Celite): 20 Alcohols more reactive than 10 alcohols. Ag2O & AgO: KMnO4: Phase transfers catalyst(Quaternary ammonium salts): Crown ether: O KMnO4/H2O/Benzene CO2H dicyclohexano 18-crown-6
  5. 5. Grc`s Collection in Organic synthesis 5 Trimethyl silyl iodide: Peterson`s synthesis: Beta hydroxyl Trimethyl silane 1,3 dithiane`s:
  6. 6. Grc`s Collection in Organic synthesis 6 DCC(di cyclo hexyl carbidoimide): DDQ(2,3 di chloro 5,6 di cyano benzo quinone): Ph Ph Ph O Ph HO O O O O O Alcoholic H2O2 : Mukaiyama reagent(N-Methyl ,2-chloro Pyridinium iodide): N Cl I-
  7. 7. Grc`s Collection in Organic synthesis 7 RuO4/CCl4 : CrO2Cl2: H2/Ni : Baker`s yeast: RMgX : Tri n-Butyl tin hydride(nBu3SnH): R-F < R-Cl < R-Br < R-I
  8. 8. Grc`s Collection in Organic synthesis 8 Gilmans reagent(R2CuLi) : LDA(Lithium di isopropyl amide): Strong base due to 20 amine & free e- pair. Satirically hindered base Wilkinson`s catalyst[Tris (tri phenyl phosphine)rhodium(I)chloride]: Hydrogenation of C=C, , with out disturbing other functional groups, It adds H2 to olifins at same side, Cis olefin to meso, Trans olefin to racemic mixture.. Palladium/H2 :
  9. 9. Grc`s Collection in Organic synthesis 9 H2/Ni useful application: Birch reduction: Pd-BaSO4(Lindlar`s catalyst): Benkeser reduction: Li0/Et2NH/Me2NH Clemmenson`s (Zn-Hg/HCl):
  10. 10. Grc`s Collection in Organic synthesis 10 Wolf kishner reduction(H2N-NH2/KOH): With di imides: With silanes: O O 3PhMe2SiH Ph CuF(PPh3)3.EtOH Ph Reduction with HCO2H: Sodium boro hydride: Reduces predominately unconjugated carbonyl compounds. Vils meier reaction: Silver tetra fluoro borate(AgBF4):
  11. 11. Grc`s Collection in Organic synthesis 11 Luche`s reagent(NaBH4-CeCl3): Reducing conjugating carbonyl compounds, Super hydride(LiBHEt3) : Sodium cyano boro hydride (NaBH3CN): Readily reduces iodides, bromides, and tosylates to the hydrocarbons... HMPA= hexa methyl phosphoramide Alanes(AlH3): DIBAL-H(Di iso butyl aluminium hydride): High temperatures: Acid derivatives to Alcohols Low temperatures: Acid derivatives to Aldehydes
  12. 12. Grc`s Collection in Organic synthesis 12 Adams catalyst (H2-PtO2): Less hindered alkenes to alkanes. Rosen mund reduction: Fremy`s salt (potassium nitroso di sulphonate) [(KO3S)2NO. ): Oxidation of phenolic derivatives to quinoids.. MnO2,DDQ and CAN : Uden friends reagent(O2+Fe+2+ascorbic acid in presence of EDTA): Gave good yields of ortho and para phenolic derivatives from phenyl acetamide. Fenton`s reagent (H2O2+Fe+2): Converts aromatic derivatives in to phenols.
  13. 13. Grc`s Collection in Organic synthesis 13 Elbs persulphate oxidation(K2S2O8/KOH): Following reagents can converts the alkenes in to their respective epoxides: NBS.H2O/NaH, TsCl/Pyridine/K2CO3/MeOH.. Ranking of peroxides: Julia colonna epoxidation: O O poly-L-Luecine/silica gel Ph Ph Urea/H2O2/DBU Hydrogen peroxide(H2O2): Asymmetric epoxidation: OsO4-NMO(N-methyl morpholine N-oxide) :
  14. 14. Grc`s Collection in Organic synthesis 14 Wood ward-Prevost hydroxylation’s: Baeyer villager epoxidation(CF3CO3H): Barbier Wieland degradation:{1)H+,EtOH,2)Excess PhMgBr,3)H3O+,4)CrO3}:2 carbon lost during the reaction LTA(Lead tetra acetate): Sodium per iodate(NaIO4):
  15. 15. Grc`s Collection in Organic synthesis 15 Selenium dioxide(SeO2): Lithium aluminium hydride(LiAlH4): Lithium tri ethoxy aluminium hydride(LiAlH(OEt)3):
  16. 16. Grc`s Collection in Organic synthesis 16 Red-Al(Sodium bis(methoxy ethoxy )aluminium hydride): *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~ "Things turn out best for the people who make the best out of the way thingsturn out."*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~Regards:Grcvr*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~