1. Grc`s Collection in Organic synthesis
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2. Grc`s Collection in Organic synthesis
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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):

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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,

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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

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Trimethyl silyl iodide:
Peterson`s synthesis: Beta hydroxyl Trimethyl silane
1,3 dithiane`s:

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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-

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RuO4/CCl4 :
CrO2Cl2:
H2/Ni :
Baker`s yeast:
RMgX :
Tri n-Butyl tin hydride(nBu3SnH):
R-F < R-Cl < R-Br < R-I

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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 :

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H2/Ni useful application:
Birch reduction:
Pd-BaSO4(Lindlar`s catalyst):
Benkeser reduction:
Li0/Et2NH/Me2NH
Clemmenson`s (Zn-Hg/HCl):

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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):

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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

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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.

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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) :

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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):

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Selenium dioxide(SeO2):
Lithium aluminium hydride(LiAlH4):
Lithium tri ethoxy aluminium hydride(LiAlH(OEt)3):

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Red-Al(Sodium bis(methoxy ethoxy )aluminium hydride):
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"Things turn out best for the people who make the best out of the way things
turn out."
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Regards:
Grcvr
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