Process for the preparation of organic compounds with imide catalysts

A process for producing an organic compound which is an addition or substitution reaction product of a compound (A) and a compound (B) or an oxidized product thereof, wherein said product is selected from the group consisting of

• (i-1) an addition reaction product or an oxidized product thereof, where an adjacent position to an oxygen atom of a compound (A1) is bonded to a carbon atom of an unsaturated bond of an unsaturated compound (B1) when an oxygen-atom-containing compound (A1) is employed as a compound (A),
• (i-2) a substitution reaction product or an oxidized product thereof, where an adjacent position to an oxygen atom of a compound (A1) is bonded to a methine carbon atom of a compound (B2) having a hydrocarbon group with a methine carbon atom when an oxygen-atom-containing compound (A1) is employed as a compound (A),
• (ii-1) an addition reaction product or an oxidized product thereof, where a bond between a carbonyl group and an atom adjacent to a carbonyl group of a compound (A2) is broken, and a group containing the a carbonyl group is bonded to the aforementioned position of a compound (B1) when a carbonyl-group-containing compound (A2) is employed as a compound (A),
• (ii-2) a substitution reaction product or an oxidized product thereof, where a bond between a carbonyl group and an atom adjacent to a carbonyl group of a compound (A2) is broken, and a group containing the a carbonyl group is bonded to the aforementioned position of a compound (B2) when a carbonyl-group-containing compound (A2) is employed as a compound (A),
• (iii-1) an addition reaction product or an oxidized product thereof, where a methine carbon atom of a compound (A3) is bonded to the aforementioned position of a compound (B1) when a compound (A3) containing a hydrocarbon group with a methine carbon atom is employed as a compound A, and
• (iii-2) a substitution reaction product or an oxidized product thereof, where a methine carbon atom of a compound (A3) is bonded to the aforementioned position of a compound (B2) when a compound (A3) containing a hydrocarbon group with a methine carbon atom is employed as a compound A,
• said process comprising the step of allowing (A) a compound capable of forming a stable radical and being selected from
• (A1) oxygen-atom-containing compounds each having a carbon-hydrogen bond at the adjacent position to an oxygen atom,
• (A2) carbonyl-group-containing compounds, and
• (A3) compounds each having a hydrocarbon group with a methine carbon atom
• to react with (B) a radical scavenging compound selected from
• (B1) unsaturated compounds, and
• (B2) compounds each having a hydrocarbon group with a methine carbon atom,
• provided that if a 1,2-dicarbonyl compound or its hydroxy reductant is used as the compound (A), the compound (B) is a radical scavenging compound (B1),
• in the presence of a catalytic imide compound and in the presence of molecular oxygen, by catalysis of the imide compound, wherein the imide compound is shown by the following formula (1):
• wherein each of R1 and R2 is, identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group, where R1 and R2 may be combined to form a double bond, or an aromatic or non-aromatic ring;
• X is an oxygen atom or a hydroxyl group;
• and one or two N-substituted cyclic imido groups indicated in the formula (1) may be further bonded to said R1, R2, or to the double bond or aromatic or non-aromatic ring formed together by R1 and R2,
• to yield a product of an addition or substitution reaction of said compound (A) and said compound (B) or an oxidized product thereof.