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  • Organic Chemistry  (9)
  • 2015-2019
  • 1995-1999  (8)
  • 1960-1964  (1)
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  • 1
    Electronic Resource
    Electronic Resource
    Enthalpies of micelle formation by hexadecyltrimethylammonium bromide in aqueous solution containing pentanol (1995)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 8 (1995), S. 108-112 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Titration calorimetric data show a dramatic change from endo- to exothermic deaggregation when pentanol-hexadecyltrimethylammonium bromide (CTAB) mixed solutions are injected into an aqueous solution containing pentanol. The results are interpreted in terms of a change in the structures of the aggregates in solution from simple CTAB micelles to mixed amphiphilic microheterogeneities when pentanol is added.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610080210
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  • 2
    Electronic Resource
    Electronic Resource
    Regioselective Reductive Ring Opening of 2-(2-Hydroxyphenyl)-3-[(trimethylsilyl)oxy]oxetanes at the More Substituted C-2 PositionDedicated to professor Ekkehard Winterfeldt on the occasion of his 65th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1529-1536 
    Details
    ISSN: 0947-3440
    Keywords: Photochemistry ; Ring opening reactions ; Oxetanes ; Reductions ; Alcohols ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compounds 7 were prepared in situ by deprotection of the corresponding pivaloyl-substituted oxetanes 3 with lithium aluminium hydride in tetrahydrofuran. under these conditions a reductive ring opening at c-2 (hydrodealkoxylation) occurred which was initiated by a nucleophilic hydride attack and which yielded the triols 8 (64-85%). the facility of the reaction and its high regioselectivity can be explained by the directing ability of the hydroxy group at the aromatic substituent. The reaction proceeds stereospecifically, as shown by deuterium labelling experiments. The prerequisite 2-(2-pivaloyloxyphenyl)-3-[(trimethylsilyl)oxy]oxetanes 3 were prepared by the Paternò-Büchi reaction of the protected salicylaldehyde 1 and various silyl enol ethers 2. The 2-hydroxyphenyl substituent at the C-3 position of oxetane 6 directed the hydride attack to the C-4 position and yielded the triol 10 in 85% yield.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970732
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  • 3
    Electronic Resource
    Electronic Resource
    Regioselective ring opening of oxetanes by hydrogenolysis. - A convenient method for the carbohydroxylation of enol ethers (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1045-1053 
    Details
    ISSN: 0947-3440
    Keywords: Photocycloaddition ; Hydrogenolysis ; Oxetanes ; Carbohydroxylation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hydrogenolysis of the 2-aryl-3-(silyloxy)oxetanes 1, 2, 5, and 9 in the presence of Pd(0) catalysts (Pd/C) yields 1,2-diols as ring-opened products almost quantitatively (82-98% yield). In combination with the preceding photocycloaddition it facilitates the regio- and stereoselective carbohydroxylation of silyl enol ethers (total yield: 43-74%). In the case of β-substituted silyl enol ethers (R1 = alkyl) the reaction sequence leads to a single diastereomeric product (4, 6, 10) in a simple two-step procedure. Acid-sensitive substrates such as the dioxolane 1g or the dihydrofuran-derived oxetane 11 are mildly cleaved in the presence of Pd(OH)2. As demonstrated by selected examples (13, 16, 18) the produced 1,2-diol remains silyl-protected if Pd(OH)2 is employed as a catalyst for the hydrogenolysis. In the latter case the silyl protective group stays at the tertiary hydroxy group to which it has been attached in the oxetane, but silyl migration may intervene as was found in the case of the sterically congested oxetane 18.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199506148
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  • 4
    Electronic Resource
    Electronic Resource
    A Short Synthesis of (±)-Oxetin (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2265-2267 
    Details
    ISSN: 0947-3440
    Keywords: Antibiotics ; Amino acids ; Photochemistry ; Oxetanes ; Protective groups ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Paternò-Büchi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971113
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  • 5
    Electronic Resource
    Electronic Resource
    Control of the J-Aggregation Phenomenon by variation of the N-alkyl-substituents (1995)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 337 (1995), S. 203-208 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyanine dyes (1a-d) with the 5,5′,6,6′-tetrachloro-1,1′-dialkyl-3,3′-di-(3-carboxypropyl)-benzimidocarbocyanine chromophore differing only in the chain length of their alkyl groups in 1,1′-position have been synthesized, spectroscopically characterized, and compared with 5,5′6,6′-tetrachloro-1,1′-diethyl-3,3′-di-(4-sulfobutyl)-benzimidocarbocyanine(TDBC). In aqueous solution the dyes form J-aggregates which, depending on the alkyl group chain length, exhibit J-bands differing in spectral positions, bandwidth, and in the number of peaks.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19953370144
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  • 6
    Electronic Resource
    Electronic Resource
    Diastereomerically Pure 3-Alkoxy- and 3-Acyloxyoxetanes from 3-silyloxyoxetanes. A case study (1996)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 338 (1996), S. 750-753 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.199633801146
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  • 7
    Electronic Resource
    Electronic Resource
    Silyl enol ethers in Paternò-Büchi reactions. Functional group tolerance and the effect of β-alkyl substitution (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 855-865 
    Details
    ISSN: 0947-3440
    Keywords: Paternò-Büchi reaction ; Oxetanes ; Diastereoselectivity ; Silyl enol ethers ; Photocycloaddition ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The photochemically induced diastereoselective formation of 3-(silyloxy)oxetanes from silyl enol ethers and aromatic aldehydes was studied. It is shown that many heteroatom- and double bond-containing substituents (ether, ester, acetal, amide, alkene) withstand the reaction conditions and may therefore be attached either to the carbonyl compound (e.g. 9) or to the silyl enol ether (e.g. 1). The formation of several functionalized oxetanes such as 2 and 11 was achieved in decent yields (42-70%). Furthermore the effect of β-substituents at the silyl enol ether was investigated. A stereoconvergent Paternò-Büchi reaction of aromatic aldehydes afforded the corresponding oxetanes (13, 16-18) in fair to excellent yields (45-87%) and with diastereoselectivities (ds) of 65-95%. No detrimental influence of the steric bulk in the β-position (R1 = Me, Et, and iPr) on the regiochemistry of the reaction was observed. Large substituents in the α-position of the enol ether [R = iPr, tBu, C(OCH2)2Et, CMe2CH=CH2] proved beneficial, isolated yields of the major diastereoisomeric oxetane ranging between 60 and 87%. The configuration of the products was elucidated by 1H-NMR spectroscopy. In the major isomer all large vicinal substituents Ar (at C-2), R (at C-3), and R1 (at C-4) at the oxetane nucleus are oriented trans to each other. The stereoselective formation of three stereogenic centers at a time can be explained by a non-concerted mechanism which invokes the intermediacy of 1,4-diradicals as intermediates.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199505124
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  • 8
    Electronic Resource
    Electronic Resource
    The Paternò-Büchi Reaction of 3-Heteroatom-Substituted Alkenes as A Stereoselective Entry to Polyfunctional Cyclic and Acyclic MoleculesDedicated to Professor G. A. Olah on the occasion of his 70th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1627-1634 
    Details
    ISSN: 0947-3440
    Keywords: Photochemistry ; Synthetic methods ; Oxetanes ; Diols ; Amino alcohols ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preparation of 3-heteroatom-substituted oxetanes by the Paternò-Büchi reaction, and their application in synthesis are reviewed. 3-Oxetanols and 3-aminooxetanes are the two most important oxetanes in this respect. By tuning the electronic properties of the enol and enamine substrates, a successful photocycloaddition to carbonyl compounds, with high yield, is possible. Since the oxetane formation proceeds stereoselectively, diastereomerically pure products are readily accessible, which can then be used in further transformations. To this end, regioselective ring-opening reactions have been developed, some of which will be discussed in this account.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970803
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  • 9
    Electronic Resource
    Electronic Resource
    Darstellung von 4-Methylchinolinen (1962)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 17 (1962), S. 63-65 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lepidin wird in einfacher Weise aus Anilinhydrochlorid, Azeton und Formalin in Gegenwart von FeCl3 mit einer Ausbeute von 40% hergestellt. Ebenso werden 6-Methyl-, 6-Methoxy- und 8-Chlorlepidin erhalten.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19620170108
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