1,2-Dicarbonyl compounds such as benzil, can be characterized by
reaction with o-phenylenediamine to form a substituted quinoxaline. See
reaction below:
a.) Write the structure for the quinoxaline derivative obtained when
benzil is the
reactant. Do you think this compound would be colored? If so, Why?
b.) Suggest a suitable mechanism for the formation of the quinoxaline
compounds based
on the above reaction scheme.
c.) What reagent would you react with o-phenylenediamine to prepare the
unsubstituted
compound quinoxaline? Show a reaction scheme giving the structure
of reactants and
products.
R
R
R
R
C = :O:
C = :O:
+
o-Phenylenediamine
(a quinoxaline)
