Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1992-12-30
1994-02-01
Lee, Mary C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
558202, C07F 942
Patent
active
052833500
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel aryl esters of phosphonous halides and to a process for the preparation thereof.
Aryl esters of phosphonous halides are valuable intermediates which, for example, are used as starting materials for the synthesis of industrially interesting phosphonous ester amides, such as are, for example, described in European Laid-Open Application 42, 359, or of phosphonous diesters.
For the preparation of such compounds, phosphonous dihalides have long been used as starting materials, which, for example, are reacted with molar amounts of an alcohol in the presence of a tertiary amine (Houben-Weyl, "Methoden der organischen Chemiell", [Methods in Organic Chemistry], Phosphorus compounds El, p. 285 (1982)).
The serious disadvantage of this process lies in the difficult preparation of the phosphonous dihalides required as precursors, as a result of which this method has not achieved industrial importance. For example, of the aromatic derivatives, only phenyldichlorophosphine is an industrially available product, by means of which alone derivatives of benzenephosphonous acid are accessible.
There was therefore considerable interest in novel aryl esters of phosphonous halides and in industrially more expedient processes for their preparation, which do not have disadvantages of this type.
The present invention relates to aryl esters of phosphonous halides of the formula I (see patent claim 1), in which a-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, naphthyl or a naphthyl radical bearing 1 to 5 substituents, where the substituents are identical or different and are a non-aromatic hydrocarbon radical, an alkoxy radical or alkylthio radical each having 1 to 8 carbon atoms, aryl or aryloxy each having 6 to 10 carbon atoms or halogen having an atomic number from 9 to 35, R.sup.2 a non-aromatic hydrocarbon radical having 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, where each aryl contains 6 to 10 carbon atoms,
With regard to industrial production, compounds having X=chlorine are clearly particularly preferred.
Furthermore, those compounds in which R.sup.1 is unsubstituted or substituted naphthyl are also particularly preferred.
In the compounds according to the invention of the formula I, R.sup.1 is for example a phenyl or benzyl radical, which bears 1 to 3 substituents, such as the C.sup.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio radical such as the alkyl radicals mentioned in detail under R2 having 1 to 8 carbon atoms and the corresponding alkoxy radicals and alkylthio radicals, or C.sub.5 -C.sub.8 -cycloalkyl, phenyl, phenoxy and/or halogen. Radicals which may specifically be mentioned are the tolyl, dimethylphenyl, trimethylphenyl, tertbutylphenyl, anisyl and naphthyl radicals, which can further bear up to 2 alkyl carbon atoms, and the various biphenyl radicals, benzyl, .alpha.-methylbenzyl and .alpha., .alpha.-dimethylbenzyl. Obviously, the substituents in R.sup.1 can only be combined in a manner such that no steric hindrance occurs. If R.sup.1 contains 3 substituents, no more than 5 carbon atoms should be contained in the two o-positions together.
Suitable R.sup.2 radicals are, for example, non-aromatic hydrocarbon radicals having 1 to 18 carbon atoms, such as alkyl or cycloalkyl, and also aromatic radicals which have 6 to 18 carbon atoms including aliphatic groups, no more than 10 carbon atoms being part of an aromatic ring system. The R.sup.2 radicals preferably contain 4 to 12 and in particular 6 to 10 carbon atoms. In detail, suitable nonaromatic hydrocarbon radicals are alkyl such as methyl, ethyl, the various propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, hexadecyl and octadecyl radicals, and cycloalkyl having 5 to 10 carbon atoms such as cyclopentyl, cyclohexyl, cycloheptyl and cyclohexylmethyl (ie. both the hydrogenated benzyl radical and also the methyl cyclohexyl radical); C.sub.8 -C.sub.10 -aryl and arylmethyl can further be mentioned, the term aryl including in each case alkylaryl, bearing at most three of the subs
REFERENCES:
patent: 3503923 (1970-03-01), Petrella et al.
patent: 4477608 (1984-10-01), Babler et al.
patent: 4751321 (1988-06-01), Mann et al.
patent: 4959406 (1990-09-01), Foltin et al.
Bohshar Manfred
Kleiner Hans-Jerg
Ambrose Michael G.
Hoechst Aktiengesellshaft
Lee Mary C.
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