Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-12-13
1996-10-29
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 48, 562899, C07D33376, C07D34500
Patent
active
055697712
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/00582 filed Apr. 6, 1994.
FIELDS OF THE INVENTION
The present inventions relate to a new substance named (haloalkyl)dibenzooniumsulfonate and its production methods; and a haloalkylating agent and haloalkylating methods.
PRIOR ART
(Haloalkyl)dibenzoonium salts and their substitution compounds are useful known haloalkylating agents for organic compounds [See Tetrahedron Lett., Vol. 31, p3579 (1990); Japanese Patent Opening No.197479/91; and J. Am. Chem. Soc., Vol. 115, p2156 (1993)].
It has, however, turned out that the known (haloalkyl)dibenzoonium salts and their substituted compounds as haloalkylating agents cause difficult problems in the post-treatment process.
For example, haloalkylating the sodium salt of 2-methyl-1, 3-cyclopentanedione with (haloalkyl)dibenzothiophenium trifluoromethanesulfonate simultaneously generate equivalent dibenzothiophene and sodium trifluoromethanesulfonate beside 2-(haloalkyl)-2-methyl-1, 3-cyclopentanedione as shown in the following formula. ##STR2##
While the latter sodium trifluoromethanesulfonate of the above-stated products can easily be removed from the reaction mixture liquid by rinsing it because that substance is water-soluble, the former dibenzothiophene cannot be separated through the rinsing process from 2-(haloalkyl)-2-methyl-1, 3-cyclopentanedione to be obtained because both substances are non-water-soluble.
As a result, a very complicated process is required to separate the dibenzothiophene from the reaction mixture liquid. This is a serious shortcoming in the prior art for this type of production.
OBJECTS OF THE INVENTIONS
The object of the present inventions is to provide new compounds suitable for industrial production from cheap materials by enabling the simpler separation of those objective products from haloalkylated substances in the post-treatment process.
CONSTITUENTS OF THE INVENTIONS
To solve the above-stated problem, the inventors have thoroughly studied an idea of integrating a water-soluble functional group into a dibenzoheterocycle. As a consequence, they succeeded in introducing (bonding) a water-soluble sulfonic acid anion group to a dibenzoheterocyclic compound. The inventors have thereby attained the object and created the present inventions.
Dibenzoheterocyclic sulfonic acid or its metallic salts which are produced by haloalkylation by means of the invented substance as the haloalkylating agent can easily be separated through the rinsing process because those products are water-soluble. Dibenzoheterocyclic sulfonic acid or its metallic salts can also be separated through the simple filtration process because they are not soluble in conventional organic solvents. ##STR3## (In the above formula, Rf, A, R.sup.1 and R.sup.2 are the same as defined in the general formula (I) of the present inventions, and M means a hydrogen atom or a metal atom.)
The present inventions relate to (haloalkyl)dibenzooniumsulfonate as represented by the following general formula (I) that is useful as a good haloalkylating agent. ##STR4## (In the above general formula, Rf means a haloalkyl group with 1 to 10 carbons; A is a sulfur atom, a selenium atom, or a tellurium atom; and R.sup.1 and R.sup.2 are hydrogen atoms, nitro groups, or lower alkyl groups with 1 to 4 carbons.)
The present inventions also provide effective methods of haloalkylating organic compounds by means of the invented haloalkylating agent.
In the above-stated general formula (I) created by these inventions, specific examples for Rf are normal chain or branching haloalkyl groups with 1 to 10 carbons (preferably fluoroalkyl groups, or particularly preferably perfluoroalkyl groups), such as: CF.sub.3, C.sub.2 F.sub.5, C.sub.3 F.sub.7, C.sub.4 F.sub.9, C.sub.5 F.sub.11, C.sub.6 F.sub.13, C.sub.7 F.sub.15, C.sub.8 F.sub.17, C.sub.9 F.sub.19, C.sub.10 F.sub.21, CHF.sub.2, C.sub.2 HF.sub.4, C.sub.3 HF.sub.6, C.sub.4 HF.sub.8, C.sub.5 HF.sub.10, C.sub.6 HF.sub.12, C.sub.7 HF.sub.14, C.sub.8 HF.sub.16, C.sub.9 HF.sub.18, C.sub.10 HF.sub.20, CH.sub.2 F, C.s
REFERENCES:
patent: 2527335 (1950-10-01), Richter et al.
Mar., "Advanced Organic Chemistry", 3rd Ed., 1985. pp. 468-470 & 473-475.
Adachi Kenji
Ishihara Sumi
Umemoto Teruo
Cebulak Mary C.
Daikin Industries Ltd.
Dees Jos,e G.
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