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.
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