Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-11-09
2003-04-15
Solola, Taofiq (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S465000
Reexamination Certificate
active
06548713
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing organic compounds such as carbonyl compounds that are useful as, for example, perfumes, paint additives, additives for resin modification, pharmaceuticals, agrochemicals, and other fine chemicals or raw materials therefor.
BACKGROUND ART
Processes for producing addition compounds are widely known, in which a radical is generated at the alpha position of an electron attractive group of a compound containing the electron attractive group, such as a ketone, and then the formed radical adds to, for example, an olefin to yield a corresponding addition compound. Metallic oxidizing agents such as Mn(III) salts have conventionally been used in this reaction. However, in this type of processes, the used metallic oxidizing agent itself is reduced to proceed an addition reaction, and the process requires a large amount of the metallic oxidizing agent and requires much effort and high cost for treating heavy metal salts after the reaction. In addition, the process using stoichiometric amounts of the metallic oxidizing agent results in low reaction selectivity and cannot significantly produce a corresponding adduct in a high yield.
DISCLOSURE OF INVENTION
Accordingly, an object of the present invention is to provide a process for efficiently producing a compound having an alkyl group or alkenyl group bonded at the alpha position of an electron attractive group, or a derivative thereof, by catalytic radical addition reaction.
Another object of the present invention is to provide a process for producing a compound having an alkyl group or alkenyl group bonded at the alpha position of an electron attractive group, or a derivative thereof, with a high selectivity from a compound having the electron attractive group, such as a ketone, and a compound having an unsaturated carbon-carbon bond.
A further object of the present invention is to provide a process for producing a ketone having an alkyl group or alkenyl group bonded at the alpha position of a carbonyl group from a hydrocarbon having a methylene group through one pot.
After intensive investigations to achieve the above objects, the present inventors have found that, when a compound of a Group 5, 6, 7, 8 or 9 element of the Periodic Table of Elements and oxygen are used in combination, they act as an oxidizing agent and a catalyst, respectively, and thereby efficiently yield a corresponding adduct from a compound having an electron attractive group and a compound having an unsaturated carbon-carbon bond (an olefin or an acetylene). The present invention has been accomplished based on these findings.
Specifically, the present invention provides a process for producing an organic compound, the process including the step of allowing a compound containing an electron attractive group represented by following Formula (1):
wherein Y is an electron attractive group; and R
b
and R
c
are each independently a hydrogen atom or an organic group, where Y, R
b
and R
c
may respectively be combined with each other to form a ring with an adjacent carbon atom, to react with a compound containing an unsaturated carbon-carbon bond represented by following Formula (2) or (7):
wherein R
d
, R
e
, R
f
, R
g
, R
i
and R
j
are each independently a hydrogen atom or an organic group, where R
d
, R
e
, R
f
and R
g
may respectively be combined with each other to form a ring with one or two adjacent carbon atoms, and R
i
and R
j
may be combined with each other to form a ring with adjacent two carbon atoms, in the presence of oxygen and a catalytic compound of a Group 5, 6, 7, 8 or 9 element of the Periodic Table of Elements to yield a compound represented by following Formula (3) or (8):
wherein Z is a hydrogen atom or a hydroxyl group; and Y, R
b
, R
c
, R
d
, R
e
, R
f
, R
g
, R
i
and R
j
have the same meanings as defined above.
The present invention also provides a process for producing an organic compound, the process including the step of allowing a carbonyl-group-containing compound represented by following Formula (1a):
wherein R
a
is a hydrogen atom or an organic group; and R
b
and R
c
are each independently a hydrogen atom or an organic group, where R
a
, R
b
and R
c
may respectively be combined with each other to form a ring with adjacent one or two carbon atoms, to react with an olefin represented by following Formula (2a)
wherein R
d
, R
e
and R
f
are each independently a hydrogen atom or an organic group; and R
g1
is an aromatic cyclic group, where R
d
, R
e
, R
f
and R
g1
may respectively be combined with each other to form a ring with one or two adjacent carbon atoms, in the presence of oxygen and a catalytic compound of a Group 5, 6, 7, 8 or 9 element of the Periodic Table of Elements to yield a furanol derivative represented by following Formula (4):
wherein R
a
, R
b
, R
c
, R
d
, R
e
, R
f
and R
g1
have the same meanings as defined above.
In addition and advantageously, the present invention provides a process for producing an organic compound, the process including the step of allowing a compound containing a methylene group represented by following Formula (5):
wherein R
b
, R
c
and R
h
are each independently a hydrogen atom or an organic group, where R
b
, R
c
and R
h
may respectively be combined with each other to form a ring with adjacent one or two carbon atoms,
to react with a compound having an unsaturated carbon-carbon bond represented by following Formula (2) or (7):
wherein R
d
, R
e
, R
f
, R
g
, R
i
and R
j
are each independently a hydrogen atom or an organic group, where R
d
, R
e
, R
f
and R
g
may respectively be combined with each other to form a ring with one or two adjacent carbon atoms, and R
i
and R
j
may be combined with each other to form a ring with adjacent two carbon atoms, in the presence of oxygen, a catalytic compound of a Group 5, 6, 7, 8 or 9 element of the Periodic Table of Elements and an imide compound represented by following Formula (6):
wherein R
1
and R
2
are the same or different and are each 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 R
1
and R
2
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 of N-substituted cyclic imido group indicated in the formula may be further formed on R
1
, R
2
, or on the double bond or aromatic or non-aromatic ring formed together by R
1
and R
2
, to yield a carbonyl compound represented by following Formula (3a) or (8a)
wherein Z is a hydrogen atom or a hydroxyl group; and R
b
, R
c
, R
h
, R
d
, R
e
, R
f
, R
g
, R
i
and R
j
have the same meanings as defined above.
The term “organic group” in the present description is used in a broad meaning including groups each containing a non-metallic atom in addition to carbon-atom-containing groups. Such groups each containing a non-metallic atom include, for example, halogen atoms, hydroxyl group, mercapto group, amino group, nitro group and sulfonic acid group.
BEST MODE FOR CARRYING OUT THE INVENTION
[Compounds Containing Electron Attractive Groups]
The compounds represented by Formula (1) for use as raw materials in the present invention include a wide variety of chain or cyclic compounds each having an electron attractive group in a molecule. Such compounds include, but are not limited to, ketones and derivatives thereof having a protected carbonyl group, aldehydes and derivatives thereof having a protected carbonyl group, esters, lactones, carboxylic acids, amides, lactams, nitrites, imino compounds and nitro compounds.
In Formula (1), electron attractive groups in Y are not specifically limited and include, for example, formyl, acetyl, propionyl, butyryl, (meth)acryloyl, cyclopentanecarbonyl, cyclohexanecarbonyl, benzoyl, naphthoyl, pyridinecarbonyl, and other aliphatic, alicyclic, aromatic or heterocyclic acyl groups and derivatives thereof having a protected carbonyl group; metho
Ishii Yasutaka
Iwahama Takahiro
Nakano Tatsuya
Sakaguchi Satoshi
Birch & Stewart Kolasch & Birch, LLP
Daicel Chemical Industries Ltd.
Solola Taofiq
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