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DI CYCLO HEXYL
CARBODIMIDE
(DCC)
DICYCLOHEXYLCARBODIMIDE
(C13H22N2)
• N,N’-Dicyclohexylcarbodimide is an organic
compound
• The important use to couple amino acids
during artificial peptide synthesis
• The compound is abbreviated as DCC, DCCD or
DCCI
PROPERTIES
• Under standard condition, it exists in the from
of white crystals with a heavy, sweet odor.
• The low melting point (30-350C)
• Boiling point 122-1240C
• Soluble in tetrahydrofuran, acetonitrile and
dimethylformamide dichloromethane, but
insoluble in water stable, but moisture
sensitive.
SAFETY PRECAUTION
• DCC is a potent allergen and a sensitizer, and
causing skin rashes.
SYNTHESIS
• It can also be prepared by oxidation of
dicyclohexylurea with p-toluene sulfonyl chloride in
hot pyridine or by heating dicyclohexylthiourea with
yellow mercuric oxide
APPLICATION
1. MOFFATT OXIDATION
• Moffatt oxidation is the oxidation of primary and secondary
alcohol in presence of dimethyl sulfoxide (DMSO) and
dicychexylcarbodimide (DCC) To form a alkoxysulfonium ylide
intermediate, which rearranges to from aldehydes and
ketones
MECHANISM
• Dicyclohexyl carbodiimide (1) is attacked by
dimethyl sulfoxide to from an intermediate (2)
• It is then promotated by the addition of the
alcohol oxygen on the sulfur atom
• Then a stable dicyclohexyl urea (4) is formed
along with sulfenate salt (3)
• It then react with a dihydeogen
phosphateanion to from ketone
THANK YOU

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Dicyclohexylcarbodiimide [DCC]

  • 2. DICYCLOHEXYLCARBODIMIDE (C13H22N2) • N,N’-Dicyclohexylcarbodimide is an organic compound • The important use to couple amino acids during artificial peptide synthesis • The compound is abbreviated as DCC, DCCD or DCCI
  • 3. PROPERTIES • Under standard condition, it exists in the from of white crystals with a heavy, sweet odor. • The low melting point (30-350C) • Boiling point 122-1240C • Soluble in tetrahydrofuran, acetonitrile and dimethylformamide dichloromethane, but insoluble in water stable, but moisture sensitive.
  • 4. SAFETY PRECAUTION • DCC is a potent allergen and a sensitizer, and causing skin rashes.
  • 5.
  • 6. SYNTHESIS • It can also be prepared by oxidation of dicyclohexylurea with p-toluene sulfonyl chloride in hot pyridine or by heating dicyclohexylthiourea with yellow mercuric oxide
  • 7. APPLICATION 1. MOFFATT OXIDATION • Moffatt oxidation is the oxidation of primary and secondary alcohol in presence of dimethyl sulfoxide (DMSO) and dicychexylcarbodimide (DCC) To form a alkoxysulfonium ylide intermediate, which rearranges to from aldehydes and ketones
  • 8.
  • 9. MECHANISM • Dicyclohexyl carbodiimide (1) is attacked by dimethyl sulfoxide to from an intermediate (2) • It is then promotated by the addition of the alcohol oxygen on the sulfur atom • Then a stable dicyclohexyl urea (4) is formed along with sulfenate salt (3) • It then react with a dihydeogen phosphateanion to from ketone
  • 10.
  • 11.