DE3447793A1 - Substituted furans and their precursors - Google Patents

Substituted furans and their precursors

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Publication number
DE3447793A1
DE3447793A1 DE19843447793 DE3447793A DE3447793A1 DE 3447793 A1 DE3447793 A1 DE 3447793A1 DE 19843447793 DE19843447793 DE 19843447793 DE 3447793 A DE3447793 A DE 3447793A DE 3447793 A1 DE3447793 A1 DE 3447793A1
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Germany
Prior art keywords
general formula
isoxazoline
protective group
hydroxyalkyl
removable protective
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Withdrawn
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DE19843447793
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German (de)
Inventor
Rainer Dr. 6702 Bad Dürkheim Becker
Walter Dr. 6909 Walldorf Himmele
Hans Dr. 6703 Limburgerhof Theobald
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Priority to DE19843447793 priority Critical patent/DE3447793A1/en
Priority to AT85116323T priority patent/ATE37362T1/en
Priority to EP85116323A priority patent/EP0187345B1/en
Priority to DE8585116323T priority patent/DE3565103D1/en
Priority to ZA859796A priority patent/ZA859796B/en
Priority to AU51679/85A priority patent/AU579693B2/en
Priority to IL77448A priority patent/IL77448A/en
Priority to HU854968A priority patent/HUT39734A/en
Priority to CA000498662A priority patent/CA1268465A/en
Priority to JP60292828A priority patent/JPS61197572A/en
Priority to DK608185A priority patent/DK168335B1/en
Publication of DE3447793A1 publication Critical patent/DE3447793A1/en
Priority to US07/384,910 priority patent/US4954633A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Furan Compounds (AREA)

Abstract

Isoxazoline of the general formula II <IMAGE> in which R<1>, R<2>, R<3> and R<4> denote unsubstituted or halogen-, haloalkyl-, alkoxy-, haloalkoxy-, nitro-, cyano-, dialkylphosphonyl- or alkoxycarbonyl-substituted alkyl, aryl, aralkyl, alkoxycarbonyl or dialkoxyphosphonyl, R<2> and R<4> also denote hydrogen and R<3> also denotes hydroxyalkyl, haloalkyl or hydroxyalkyl masked by a removable protective group, X denotes hydrogen or a removable protective group, and processes for the preparation of furans from the isoxazoles.

Description

Substituierte Furane und deren VorDrodukteSubstituted furans and their precursors

Bis zu vierfach substituierte Furane der allgemeinen Formel (I) in der R1 bis R4 die in den vorstehenden Ansprüchen angegebene Bedeutung haben, werden als Vorprodukte, z.B. für die Herstellung von Pflanzenschutzmitteln benötigt: Es ist bekannt, daß Furane aus 1,4-Diketonen durch Cyclisierung hergestellt werden können (Comprehensive Heterocyclic Chemistry Vol. 4 657 ff, (1984). Bei der Synthese von insbesondere asymmetrisch substituierten Furanen (z.B. 2.4-Disubstitution) ist die Herstellung der erforderlichen Ausgangsprodukte schwierig. Aus diesem Grunde werden beispielsweise für die Herstellung von 2-Benzyl-4-hydroxymethylfuran, einem gesuchten Zwischenprodukt für Insektizidsynthesen, verschiedene Verfahren empfohlen (CS (c) 1971, 2551; Wegler Vol. 7 (1981) S. 76; DOS 21 22 823). Alle diese Verfahren weisen jedoch schwerwiegende Nachteile auf (vielstu.fige Synthesen mit mäßiger Gesamtausbeute, Sicherheitsprobleme durch hohe Temperaturen, Isomerenbildung).Up to four times substituted furans of the general formula (I) in which R1 to R4 have the meaning given in the preceding claims, are required as precursors, e.g. for the production of crop protection agents: It is known that furans can be produced from 1,4-diketones by cyclization (Comprehensive Heterocyclic Chemistry Vol. 4 657 ff, (1984). In the synthesis of, in particular, asymmetrically substituted furans (eg 2,4-disubstitution), it is difficult to prepare the necessary starting materials Insecticide syntheses, various methods recommended (CS (c) 1971, 2551; Wegler Vol. 7 (1981) p. 76; DOS 21 22 823). However, all these methods have serious disadvantages (multi-stage syntheses with a moderate overall yield, safety problems due to high temperatures, isomer formation).

Es ist eine Aufgabe der Erfindung. ein Verfahren zur Herstellung substituierter Furane anzugeben, das mit leicht zugänglichen Ausgangsstoffen auskommt und leicht durchzuführen ist.It is an object of the invention. a process for the preparation of substituted To indicate furans that get by with easily accessible starting materials and are easy is to be carried out.

Es wurde gefunden, daß man Furane der vorgenannten Art vorteilhaft dadurch erhält, daß man ein entsprechendes Isoxazolin der Formel II in der X Hydroxy, Halogen oder durch eine abspaltbare Schutzgruppe verkappter Hydroxy bedeutet, hydriert. Isoxazoline der allgemeinen Formel II sind neue Stoffe. Es versteht sich, daß in den Fällen. wo sowohl R3 ein verethertes oder verestertes Hydroxymethyl als auch X verkapptes Hydroxy bedeutet, eine Veretherung bzw. Veresterung mit einem jeweils bifunktionellen Partner unter Ringbildung stattgefunden haben kann. Abhängig von der speziellen Verfahrensweise kann dies direkt geschehen oder es kann als Zwischenstufe das Hydroxyketon III isoliert und in einem anschließenden Schritt das gewünschte Furanderivat I erhalten werden: Für den Fall des oben erwähnten 2-Benzyl-4-hydroxymethylfurans läßt sich die Umsetzung wie folgt wiedergeben: Zur Herstellung der neuen Vorprodukte II ist insbesondere das folgende zu sagen: Isoxazoline II können z.8. nach der Methode in Heterocycles. Bd. 12, S. 1243 ff. (1979) durch Umsetzen von Nitriloxiden mit bestimmten Olefinen erhalten werden nach In der vorstehenden Umsetzung bedeutet X Hydroxy oder durch eine abspaltbare Schutzgruppe, z.B. t-8utyl, Trimethylsilyl, Acetyl, Benzyl. verkapptes Hydroxy. Es lassen sich im übrigen manche der erfindungsgemäßen Isoxazoline aus anderen, nach der vorstehenden Methode zugänglichen Isoxazolinen erhalten: z.ß. kann in 3-Stellung substituiertes 5,5-Bis-hydroxymethylisoxazolin an den HydroxygTuppen mit den vorgenannten Schutzgruppen versehen oder diese abgespalten werden oder z.B. Hydroxy und Halogen oder Halogen und eine Schutzgruppe gegeneinander ausgetauscht werden.It has been found that furans of the aforementioned type are advantageously obtained by using a corresponding isoxazoline of the formula II in which X is hydroxy, halogen or hydroxy blocked by a removable protective group, hydrogenated. Isoxazolines of the general formula II are new substances. It goes without saying that in the cases. where both R3 denotes an etherified or esterified hydroxymethyl and X denotes a capped hydroxy, an etherification or esterification with a bifunctional partner in each case with ring formation may have taken place. Depending on the specific procedure, this can be done directly or the hydroxyketone III can be used as an intermediate isolated and the desired furan derivative I can be obtained in a subsequent step: In the case of the above-mentioned 2-benzyl-4-hydroxymethylfuran, the reaction can be reproduced as follows: The following should be said in particular about the production of the new precursors II: Isoxazoline II can e.g. 8. according to the method in Heterocycles. Vol. 12, p. 1243 ff. (1979) obtained by reacting nitrile oxides with certain olefins according to In the above reaction, X denotes hydroxy or a removable protective group, for example t-8utyl, trimethylsilyl, acetyl, benzyl. capped hydroxy. In addition, some of the isoxazolines according to the invention can be obtained from other isoxazolines obtainable by the above method: e.g. 5,5-bis-hydroxymethylisoxazoline substituted in the 3-position can be provided with the aforementioned protective groups on the hydroxy groups or these can be split off or, for example, hydroxy and halogen or halogen and a protective group can be exchanged for one another.

Die als Ausgangsstoffe benötigten Nitriloxide können ihrerseits z.B. aus entsprechenden Oximen erhalten werden oder aus aliphatischen Nitroverbindungen.The nitrile oxides required as starting materials can in turn e.g. can be obtained from corresponding oximes or from aliphatic nitro compounds.

Es wird hierzu auf Heterocycles, a.a.O. und die dort aufgeführten Literaturhinweise, ferner auf Houben-Weyl, Methoden. 14. Aufl. Band 10/3, S. 83? und auf J.Org.Chem. 28, 1150 (1963) verwiesen.For this, reference is made to Heterocycles, op. Cit. And those listed there References, also on Houben-Weyl, methods. 14th ed. Volume 10/3, p. 83? and on J.Org.Chem. 28, 1150 (1963).

Die Isolierung der Nitriloxide der Formel tJ ist nicht unbedingt erforderlich. Sie werden vorteilhaft gleich in Anwesenheit der Alkenylverbindungen erzeugt, mit denen sie sich ummittelbar zu den Isoxazolinen der Formel II umsetzen.The isolation of the nitrile oxides of the formula tJ is not absolutely necessary. They are advantageously generated immediately in the presence of the alkenyl compounds, with which they convert directly to the isoxazolines of the formula II.

Die zur Darstellung der Isoxazoline verwendeten Nitriloxide und die Alkenylverbindungen können in äquimolaren Verhältnissen oder jeweils einer der Reaktionspartner im Überschuß eingesetzt werden.The nitrile oxides used to prepare the isoxazolines and the Alkenyl compounds can be used in equimolar proportions or in each case one of the reactants be used in excess.

Als Lösungsmittel fur die Umsetzung eignet sich z.8. die jeweilige Alkenylverbindung selbst, ferner aromatische Verbindungen (z.B. Benzol, Toluol Xylol}, halogenierte aromatische Verbindungen, Ketone (z.B.A suitable solvent for the reaction is e.g. the respective Alkenyl compound itself, also aromatic compounds (e.g. benzene, toluene xylene}, halogenated aromatic compounds, ketones (e.g.

Aceton, Methylethylketon, Diisopropylketon). Ether (z.B. Dioxan, Diethylether, THF), chlorierte aliphatische Kohlenwasserstoffe (z.8. Dichlorethan, Chloroform, Methylenchlorid).Acetone, methyl ethyl ketone, diisopropyl ketone). Ethers (e.g. dioxane, diethyl ether, THF), chlorinated aliphatic hydrocarbons (e.g. dichloroethane, chloroform, Methylene chloride).

Es ist darauf hinzuweisen, daß die Anlagerung der Olefine an diese Nitriloxide je nach der Art der Substituenten verläuft und daher u.U.It should be noted that the addition of the olefins to these Nitrile oxides, depending on the nature of the substituents, and therefore under certain circumstances

Isomere bzw. Gemische von Isomeren erwartet werden können. Als allgemeine Regel ist anzunehmen, daß die an das Sauerstoffatom des Nitriloxids angelagerte Seite der olefinischen Bindung diejenige ist, die den - rãumlich - größeren Substituenten trägt.Isomers or mixtures of isomers can be expected. As a general As a rule it can be assumed that the attached to the oxygen atom of the nitrile oxide The side of the olefinic bond is that which has the - spatially - larger substituent wearing.

Alle vorstehend beschriebenen Umsetzungen verlaufen gewöhnlich unterhalb von etwa 1500C mit ausreichender Geschwindigkeit.All of the reactions described above usually proceed below of about 1500C with sufficient speed.

HerstellbeisDiel für ein Isoxazolin 159 g Phenylacetaldoxim und 202,5 g Isobutylendiacetat werden in 500 ml Diethylether gelöst und unter starkem Rühren bei 10 bis 150C mit 1 050 ml einer 10eigen Natriumhypochloritlösung versetzt. Nach mehrstundigem Rühren wird die organische Phase mit Wasser ausgeschüttelt über Natriumsulfat getrocknet und vom Lösungsmittel befreit.Manufacturing example for an isoxazoline 159 g of phenylacetaldoxime and 202.5 g of isobutylene diacetate are dissolved in 500 ml of diethyl ether and, with vigorous stirring at 10 to 150 ° C., 1050 ml of a 10% sodium hypochlorite solution are added. After stirring for several hours, the organic phase is extracted by shaking with water, dried over sodium sulfate and freed from the solvent.

-Ausbeute 333 g - 92,8X der berechneten Menge. Kristalle aus Ethanol-Petrolether schmelzen bei 78 bis 790C.- Yield 333 g - 92.8X the calculated amount. Ethanol petroleum ether crystals melt at 78 to 790C.

Beispiel für die Herstelluna eines Furans 88.4 g 3-Benzyl-5,5-bis(hydroxymethyl)isoxazolin werden in 550 ml Tetrahydrofuran, 40 ml Wasser und 80 ml Eisessig aufgenommen und mit 1,6 g Platinoxid versetzt. Beim Einleiten von Wasserstoff setzt eine leicht exotherme Reaktion ein; nach beendeter Wasserstoffaufnahme wird abfiltriert, eingeengt und der Rückstand mit Aceton verrührt. Das ungelöste Ammoniumacetat wird abfiltriert, das Filtrat wieder eingeengt kund dann in 300 ml Methylenchlorid mit 300 ml 1obiger Salzsäure eine Stunde bei 200C verrührt. Dann wird die Lösung in Methylenchlorid abgetrennt, mit Wasser gewaschen und eingeengt. Es verbleiben 59,2 g 2-Benzyl-4-hydroxymethylfuran NMR-spektroskopisch praktisch rein (79Z bezogen auf Isoxazolin). Destillation (0,3 mm1125-1280) liefert 52,0 g einer Substanz mit einem Schmelzpunkt von 37 bis 380C).Example for the production of a furan 88.4 g of 3-benzyl-5,5-bis (hydroxymethyl) isoxazoline are taken up in 550 ml of tetrahydrofuran, 40 ml of water and 80 ml of glacial acetic acid and added 1.6 g of platinum oxide. When introducing hydrogen, one sets easily exothermic reaction on; after the uptake of hydrogen has ended, it is filtered off and concentrated and the residue is stirred with acetone. The undissolved ammonium acetate is filtered off, the filtrate was concentrated again and then dissolved in 300 ml of methylene chloride with 300 ml of 1obiger Hydrochloric acid stirred for one hour at 200C. Then the solution is in methylene chloride separated, washed with water and concentrated. 59.2 g of 2-benzyl-4-hydroxymethylfuran remain Practically pure according to NMR spectroscopy (79Z based on isoxazoline). Distillation (0.3 mm1125-1280) provides 52.0 g of a substance with a melting point of 37 to 380C).

Claims (4)

PatentansDrüche 1. Isoxazolin der allgemeinen Formel II in der R1, R2. R3 und R4 unsubstituiertes oder durch Halogen, Haloalkyl, Alkoxy. Haloalkoxy, Vitro Cyan, Dialkylphosphonyl oder Alkoxycarbonyl substituiertes Alkyl, Aryl, Aralkyl, Alkoxycarbonyl oder Dialkoxyphosphonyl. R2 und R4 auch Wasserstoff und R3 auch Hydroxyalkyl oder durch eine abspaltbare Schutzgruppe verkapptes Hydroxyalkyl, X Hydroxy, Halogen oder durch eine abspaltbare Schutzgruppe verkapptes Hydroxy bedeutet.Claims 1. Isoxazoline of the general formula II in the R1, R2. R3 and R4 are unsubstituted or by halogen, haloalkyl, alkoxy. Haloalkoxy, vitro cyano, dialkylphosphonyl or alkoxycarbonyl substituted alkyl, aryl, aralkyl, alkoxycarbonyl or dialkoxyphosphonyl. R2 and R4 also denote hydrogen and R3 also denote hydroxyalkyl or hydroxyalkyl capped by a removable protective group, X denotes hydroxy, halogen or hydroxyl capped by a removable protective group. 2. Verfahren zur Herstellung von Isoxazolinen der allgemeinen Formel I, dadurch gekennzeichnet daß man in an sich bekannter Weise ein entsprechendes Nitrooxid R1CNO mit einer entsprechenden, olefinisch ungesättigten Verbindung R2HC=CR3(CHR4X) umsetzt.2. Process for the preparation of isoxazolines of the general formula I, characterized in that one in a known manner a corresponding Nitro oxide R1CNO with a corresponding, olefinically unsaturated compound R2HC = CR3 (CHR4X) implements. 3. Verwendung der Isoxazoline der allgemeinen Formel II in einem Verfahren zur Herstellung entsprechender Furane der allgemeinen Formel I dadurch gekennzeichnet. daß man das Isoxazolin hydriert.3. Use of the isoxazolines of the general formula II in a process for the preparation of corresponding furans of the general formula I. characterized. that the isoxazoline is hydrogenated. 4. Verwendungsverfahren nach Anspruch 3 dadurch gekennzeichnet. daß man die Hydrierung unter nicht-sauren Bedingungen vornimmt. ein entsprechendes Hydroxyketon der allgemeinen Formel III R1CO-CHR2-C(OH)R3-CH(X)R4 (III) als Zwischenprodukt gewinnt und dieses durch Ansäuern in das Furan überführt.4. Use method according to claim 3, characterized. that the hydrogenation is carried out under non-acidic conditions. a corresponding hydroxyketone of the general formula III R1CO-CHR2-C (OH) R3-CH (X) R4 (III) wins as an intermediate and this is converted into the furan by acidification.
DE19843447793 1984-12-29 1984-12-29 Substituted furans and their precursors Withdrawn DE3447793A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DE19843447793 DE3447793A1 (en) 1984-12-29 1984-12-29 Substituted furans and their precursors
AT85116323T ATE37362T1 (en) 1984-12-29 1985-12-20 SUBSTITUTED FURANS AND THEIR PRECURSORS.
EP85116323A EP0187345B1 (en) 1984-12-29 1985-12-20 Substituted furanes and their precursors
DE8585116323T DE3565103D1 (en) 1984-12-29 1985-12-20 Substituted furanes and their precursors
ZA859796A ZA859796B (en) 1984-12-29 1985-12-23 Substituted furans and their precursors
AU51679/85A AU579693B2 (en) 1984-12-29 1985-12-24 Novel substituted isoxazolines as precursors for substituted furans
IL77448A IL77448A (en) 1984-12-29 1985-12-25 Preparation of substituted furans and novel isoxazolines used as starting materials therefor
HU854968A HUT39734A (en) 1984-12-29 1985-12-27 Process for preparing furan derivatives
CA000498662A CA1268465A (en) 1984-12-29 1985-12-27 Isoxazolines useful in preparing furans
JP60292828A JPS61197572A (en) 1984-12-29 1985-12-27 Manufacture of substituted furan and precursor therefor
DK608185A DK168335B1 (en) 1984-12-29 1985-12-30 Process for the preparation of substituted furan compounds and isoxazolines for use therewith
US07/384,910 US4954633A (en) 1984-12-29 1989-07-25 Isoxazolines as intermediates to furans

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4954633A (en) * 1984-12-29 1990-09-04 Basf Aktiengesellschaft Isoxazolines as intermediates to furans

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20010914A1 (en) * 2001-05-04 2002-11-04 Endura Spa PROCESS FOR THE PRODUCTION OF 5-BENZYL-3-FURFURYL ALCOHOL

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4954633A (en) * 1984-12-29 1990-09-04 Basf Aktiengesellschaft Isoxazolines as intermediates to furans

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JPS61197572A (en) 1986-09-01

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