Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1990-10-25
1992-06-02
Stoll, Robert L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
570127, 570144, 568927, C07C 1704, C07C 2208, C07C20506
Patent
active
051188791
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel fluoroalkyl derivative and a process for preparing the same.
BACKGROUND TECHNOLOGY
Compounds in which fluoroalkyl groups are introduced into organic compounds attract public attention in recent years as they have physiological activities or like functions. Particularly, the compounds having the thus introduced fluoroalkyl groups have been known as intermediates for the synthesis of medicinal and agricultural chemicals and water- and oil-repellent agents.
However, fluoroalkyl derivatives represented by the following general formulae (IV) and (V) of: ##STR3## (In the formulae, L.sub.1 stands for an aryl or alkyl group, L.sub.2 stands for a hydrogen atom or a methyl group. And n stands for an integer of from 1 to 20.), i.e. fluoroalkyl group-containing chlorinated compounds, fluoroalkyl group-containing unsaturated compounds derived therefrom and the process for preparing the same, have not yet been known up to date.
An object of this invention is to provide fluoroalkyl derivatives which are utilizable as the intermediates for the synthesis of medicinal and agricultural chemicals and water- and oil-repellents, and to provide a process for preparing the same.
Another object of this invention is to provide a process for preparing a fluoroalkyl derivative easily at high yield without using any special device.
DISCLOSURE OF THE INVENTION
According to the present invention, there is provided a fluoroalkyl derivative represented by the following general formula (I) of ##STR4## (In the formula, R.sub.1 stands for ##STR5## (where X stands for a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a nitro group), an aroyloxy group, or an alkyl or alkoxycarbonyl group having 1 to 20 carbon atoms, and R.sub.2 stands for a hydrogen atom or a methyl group. Meantime, n stands for an integer of from 1 to 20.)
Also provided by the present invention is a fluoroalkyl derivative represented by the following general formula (II) of the preceding general formula (I).)
Further provided by the present invention is a process for preparing a fluoroalkyl derivative represented by the aforementioned general formula (I) or fluoroalkyl derivatives represented by the aforementioned general formulae (I) and (II), comprising reacting an olefin compound represented by the following general formula (III) of: preceding general formula (I).) (IV) of: metal catalyst.
Further provided by the present invention is a process for preparing a fluoroalkyl derivative represented by the aforementioned general formula (II), comprising reacting an olefin compound represented by the aforementioned general formula (III) with a fluoroalkanesulfonyl chloride represented by the general formula (IV) in the presence of a metal catalyst to obtain a compound represented by the general formula (I), and then treating the compound (I) with an alkali.
BEST EMBODIMENTS FOR THE PRACTICE OF THE INVENTION
The present invention will be described more in detail hereinbelow.
The fluoroalkyl derivatives of the invention may be represented by the following general formulae (I) and (II) of: ##STR6## (In the formulae, R.sub.1 stands for ##STR7## (where X stands for a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a nitro group), an aroyloxy group, or an alkyl or alkoxycarbonyl group having 1 to 20 carbon atoms, and R.sub.2 stands for a hydrogen atom or a methyl group. Meantime, n stands for an integer of from 1 to 20.) It is difficult to prepare those each including R.sub.1 which is an alkyl group having not less than 21 carbon atoms.
Preferable examples of the fluoroalkyl derivatives represented by the aforementioned general formula (I) include: 1-phenyl-1-chloro-3,3,3-trifluoropropane, 1-phenyl-1-chloro-2-methyl-3,3,3-trifluoropropane, 1-p-chlorophenyl-1-chloro-3,3,3-trifluoropropane, 1-p-tolyl-1-chloro-2-methyl-3,3,3
REFERENCES:
patent: 3326928 (1967-06-01), Mattson
Umemoto et al., Tetrahedron Letters, vol. 23, No. 11, pp. 1169-1172, 1982.
Kamigata et al. Phosphorus Sulfur, 19(2), 199-203, 1984; CA 101:72368c.
Dmowski, J. Fluorine Chem., 29(3), 287-96, 1985. CA105:97073y.
Minnesota Mining & Manufg. Co., CA 55:16452c, 1961.
Fuchikami et al., Tetrahedron Letters, 25(3), 303-6, 1986. CA100:209096.
Thaoi et al., J. Fluorine Chem., 6(4), 311-29, 1975. CA83:177764s.
Umemoto et al., Tetrahedron Letters, vol. 23, No. 35, PP3579-82, 1982.
Kamigata Nobumasa
Nakayama Masaharu
Sawada Hideo
Yoshida Masato
Nippon Oil and Fats Co. Ltd.
Sayala C.
Stoll Robert L.
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