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  • Organic Chemistry  (15)
  • General Chemistry  (2)
  • Benzyloxy-benzoyl transformation  (1)
  • Dimerization  (1)
  • Garugamblin-2  (1)
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  • 1
    Electronic Resource
    Electronic Resource
    Oxidation of o-Methoxyphenols with a Hypervalent Iodine Reagent: Improved Synthesis of Asatone and Demethoxyasatone (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2579-2581 
    Details
    ISSN: 1434-193X
    Keywords: Hypervalent iodine ; Phenols ; Oxidation ; Cyclohexa-2,4-dienones ; Dimerization ; Asatone ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4c-f, which dimerized spontaneously to a single product (5c-f) in each case. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol derivatives 1a and 1b, respectively.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of Acerogenin C and (+)-Acerogenin A, Two Macrocyclic Diarylheptanoid Constituents of Acer nikoense (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 521-524 
    Details
    ISSN: 1434-193X
    Keywords: Acerogenin C ; (+)-Acerogenin A ; Synthesis ; Diarylheptanoids, macrocyclic ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The macrocyclic ketone acerogenin C (3) and the corresponding alcohol (+)-accerogenin A (1), diarylheptanoid constituents of the maple Acer nikoense were synthesized. The key steps were the selective reduction of the double bond of an α,β-unsaturated ketone (10) and macrocyclization of an iodophenol (13) by a modified Ullmann diarylether synthesis.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Oxidation von 1,3-Diphenyl-1,3-propandionen mit Thallium-(III)-nitrat in Methanol (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1271-1282 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidation of 1,3-Diphenyl-1,3-propanediones with Thallium(III) Nitrate in MethanolOn oxidation with thallium(III) nitrate in methanol, 1,3-diphenyl-1,3-propanediones 1 rearrange to give 3-oxo-2,3-diphenylpropanoic esters 2 and products derived therefrom. However, 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones 1h-k undergo oxidative cyclization to 2-aroyl-3(2H)-benzofuranones 5. The alkali and acid catalysed cleavage of 5 is discussed.
    Notes: Bei der Oxidation mit Thallium(III)-nitrat in Methanol werden die 1,3-Diphenyl-1,3-propandione 1 zu den 3-Oxo-2,3-diphenylpropansäureestern 2 und deren Folgeprodukte umgelagert. Die 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propandione 1h-k werden dagegen oxidativ zu den 2-Aroyl-3(2H)-benzofuranonen 5 cyclisiert.  -  Der durch Alkalilauge und Säure katalysierte Abbau von 5 wird diskutiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800811
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese der Pterocarpane aus Swartzia laevicarpa (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 127-132 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Pterocarpan Constituents of Swartzia laevicarpaThe synthesis of 2,8-dihydroxy-3,4-dimethoxy- (1), 2,8-dihydroxy-3,9,10-trimethoxy- (2), 8-hydroxy-3,4,9,10-tetramethoxy- (3), and 2,8-dihydroxy-3,4,9,10-tetramethoxypterocarpan (4)  -  each of them as racemate  -  confirmed the constitution of four new pterocarpans isolated from Swartzia laevicarpa.
    Notes: Durch die eindeutige Synthese von jeweils racemischem 2,8-Dihydroxy-3,9-dimethoxy- (1), 2,8-Dihydroxy-3,9,10-trimethoxy-(2), 8-Hydroxy-3,4,9,10-tetramethoxy-(3) und 2,8-Dihydroxy-3,4,9,10-tetramethoxypterocarpan (4) wurde die Konstitution von vier neuen, aus Swartzia laevicarpa isolierten Pterocarpanen bestätigt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840113
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  • 5
    Electronic Resource
    Electronic Resource
    Eine einfache Methode zur Herstellung von 2-Arylbenzofuranen und die Synthese von Moracin A und B (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 734-741 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Practical Method for the Preparation of 2-Arylbenzofurans and the Synthesis of Moracin A and BOxidative rearrangement of 2-benzyloxychalcones 2 with Ti(No3)3 in methanol to 1,2-diaryl-3,3-dimethoxy-1-propanones 3, alkaline degradation to aryl 2-benzyloxybenzyl ketones 4, debenzylation, and ring closure gave 2-arylbenzofurans 1. In this way moracin A and B (1a, b), further 2-(2,4-dihydroxyphenyl_-5,6-dimethoxybenzofuran (1c) were synthesized. The latter was not identical with a substance isolated from Myroxylon balsamum for which structure 1c was claimed.
    Notes: Die oxidative Umalgerung von 2-Benzyloxychalkonen J. Amer. Chem. Soc.2 mit Ti(NO3)3 in Methanol, alkalischer Abbau der entstandenen 1,2-Diaryl-3,3-dimethoxy-1-propanone 3 zu Aryl(2-benzyloxybenzyl)-ketonen 4, Entbenzylierung und Ringschluß führte zu 2-Arylbenzofuranen 1. Mit dieser Methode wurden u. a. Moracin A und b (1a, b) sowie 2-(2,4-Dihydroxyphenyl)-5,6-dimethoxybenzofuran (1c) synthetisiert. Letzteres war mit einer aus Myroxylon balsamum isolierten und als 1c beschriebenen Substanz nicht identisch.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840410
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  • 6
    Electronic Resource
    Electronic Resource
    Synthese des rac-5′-O-Methylphaseollinisolfavans (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 2179-2181 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of rac-5′-O-methylphaseollinisoflavanThe title substance 2 and its isomer 9 were synthesized from 4′,7-dihydroxy-2′-methoxy-isoflavone (4) in five steps.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619861211
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese der natürlichen Isoflav-3-ene Haginin A, B und D (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 555-558 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Natural Isoflav-3-enes Haginin A, B, and DThe synthesis of the title isoflav-3-enes haginin A (1), haginin B (2), and haginin D (4) as well as that of the isoflavan-4-one rac-lespedeol C (22) and of the pterocarpanes rac-nissolin (20) and rac-methylnissolin (21) by reduction of the corresponding isoflavones is described.
    Notes: Die Synthese der Isoflav-3-ene Haginin A (1), Haginin B (2) und Haginin D (4) sowie des Isoflavan-4-ons rac-Lespedeol C (22) und der Pterocarpane rac-Nissolin (20) und rac-Methylnissolin (21) durch Reduktion der entsprechenden Isoflavone wird beschrieben.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880611
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  • 8
    Electronic Resource
    Electronic Resource
    Oxidative Umlagerung von α-Benzylidenketonen mit Thallium(III)-nitrat in Methanol (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1283-1295 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidative Rearrangement of α-Benzylideneketones with Thallium(III) Nitrate in MethanolSterically unhindered arylidene- and diarylideneacetones 1 or 2 having electron releasing aryl groups yielded with thallium(III) nitrate in methanol β-ketoacetals 3, 4 and 5, respectively. Electronegatively substituted 1f and sterically hindered 1g and 1h gave the 4-arylcrotonic esters 7 and by-products, while 1,3-dibenzylidenacetone (2a) yielded besides the expected products also the branched acetal esters 13a and 13b. Formation of the anomalous products 7 and 13 can be rationalized assuming a common cyclopropanone type intermediate.
    Notes: Sterisch unbehinderte Aryliden- und Diarylidenacetone 1 bzw. 2 mit elektronenspendenden Aryl-gruppen liefern mit Thallium(III)-nitrat in Methanol die β-Ketoacetale 3, 4 bzw. 5. Das elektronegativ substituierte 1f sowie die sterisch gehinderten Acetonderivate 1g und 1h ergeben die 4-Arylcrotonsäureester 7 und Nebenprodukte, während aus 1,3-Dibenzylidenaceton (2a) neben den erwarteten Produkten auch die verzweigten Acetalester 13a und 13b entstehen. Für die Bildung der anomalen Produkte 7 und 13 wird als gemeinsames Zwischenprodukt ein Cyclopropanonderivat vorgeschlagen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800812
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  • 9
    Electronic Resource
    Electronic Resource
    Synthese von Marchantin I, einem macrocyclischen Bis(bibenzylether) aus Riccardia multifida (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1141-1143 
    Details
    ISSN: 0170-2041
    Keywords: Liverwort ; Macrocyclic ether ; Marchantin I ; Riccardia multifida ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Marchantin I, a Macrocyclic Bis(bibenzyl Ether) from Riccardia multifidaThe unambigous synthesis of marchantin (1), a bis(bibenzyl ether) with a 18-membered ring, by Ullmann, Wittig, and modified Wurtz reaction is reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890284
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  • 10
    Electronic Resource
    Electronic Resource
    Synthese von Pakyonol, einem macrocyclischen Bis(bibenzylether) aus Mannia fragrans (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 299-301 
    Details
    ISSN: 0170-2041
    Keywords: Pakyonol ; Mannia fragrans ; Liverwort ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Pakyonol, a Macrocyclic Bis(bibenzyl ether) from Mannia fragransThe unambigous synthesis of pakyonol (1), a bis(bibenzyl ether) with a 20-membered ring by Ullmann, Wittig, and modified Wurtz reaction is reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900155
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