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  • 1
    Electronic Resource
    Electronic Resource
    Chemie reaktiver Kationen von Schwefeldioxidanalogen, IV. N-Methyl-N-sulfinylmethanaminiumsalze  -  Umsetzungen mit Carbonyl- und Thiocarbonylverbindungen (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 65-69 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemistry of Reactive Cations Derived from Sulfur Dioxide Analogues, IV1).  -  N-Methyl-N-sulfinylmethanaminium Salts  -  Reactions with Carbonyl and Thiocarbonyl CompoundsN-Methyl-N-sulfinylmethanaminium tetrafluoroborate (1) reacts with aromatic aldehydes by elemination of SO2 to form the imonium salts 3, with thiones, dithiocarboxylic, and trithiocarbonic acid derivatives by formal loss of S2O to give the imonium salts 5, 7, 10, and 12. The rotation barrier around the CN bond has been determined for 10 as 69.5 and for 12 as 77.8 kJ/mol.
    Notes: N-Methyl-N-sulfinylmethanaminium-tetrafluoroborat (1) reagiert mit aromatischen Aldehyden unter SO2-Abspaltung zu den Imoniumsalzen 3, mit Thionen, Dithiocarbonsäure- und Trithio-kohlensäurederivaten unter formaler Abspaltung von S2O zu den Imoniumsalzen 5, 7, 10 und 12. Die Rotationsbarriere um die CN-Bindung wird für 10 zu 69.5 und für 12 zu 77.8 kJ/mol bestimmt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810112
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  • 2
    Electronic Resource
    Electronic Resource
    Influence of enol acetylation on the photo-fries rearrangement of an ortho-acylaryl benzoate (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 2238-2243 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Einfluß der Enol-Acetylierung auf die Photo-Fries-Umlagerung eines Benzoesäure-ortho-acylarylestersDas Enolacetat 1b erleidet bei Bestrahlung Spaltung der Benzoyl-Sauerstoff-Bindung, wobei eine Mischung der Benzophenone 4 und 5 resultiert. Die primär entstehenden Photo-Fries-Produkte 2 und 3 konnten infolge einer schnellen intramolekularen Umacetylierung nicht isoliert werden. Das Acetophenon 6 lagert sich unter den gleichen experimentellen Bedingungen zu den Benzophenonen 7 und 8 um, jedoch sind die Ausbeuten bemerkenswert niedriger als im obigen Fall. Die Verbindungen 7 und 8 werden durch Acetanhydrid in Gegenwart von Pyridin in die jeweiligen Essigsäureester 4 und 5 übergeführt.
    Notes: The enol acetate 1b undergoes benzoyl-oxygen bond rupture upon irradiation, giving a mixture of benzophenones 4 and 5. The primary photo-Fries products 2 and 3 could not be isolated, due to a rapid intramolecular transacetylation. The acetophenone 6 rearranges to give the benzophenones 7 and 8 under the same conditions, but the yields are significantly lower than in the former case. Compounds 7 and 8 are separately correlated with 4 and 5 by treatment with acetic anhydride in the presence of pyridine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219821214
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  • 3
    Electronic Resource
    Electronic Resource
    Alkylierungsprodukte von Sulfinen und ThionimidenHerrn Prof. Dr. G. Manecke zum 65. Geburtstag gewidmet. (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1505-1509 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Alkylation Products of Sulfines and Thione ImidesMethyl 2,4,6-trimethyldithiobenzoate S-oxide as well as sulfines (thione oxides) and thione imides derived from 3H-1,2-dithiol-3-thiones are alkylated by trimethyloxonium salts to give stable O-or N-alkyl derivatives, respectively.
    Notes: 2,4,6-Trimethyldithiobenzoesäure-methylester-S-oxid (2b) sowie die von 3H-1,2-Dithiol-3-thionen abgeleiteten Sulfine (Thionoxide) und Thionimide ergeben stabile Alkylierungsprodukte mit Trimethyloxoniumsalzen. Die Alkylierung erfolgt am O- bzw. N-Atom.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810822
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  • 4
    Electronic Resource
    Electronic Resource
    3H-1,2-Dithiol-3-thion-S-oxideHerrn Prof. Dr. G. Manecke zum 65. Geburtstag gewidmet. (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1510-1512 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 3H-1,2-Dithiol-3-thione-S-oxidesThe sulfines 4 are synthetized by oxidation of the corresponding trithiones 1. The properties of 4 are described.
    Notes: Durch Oxidation der Trithione 1 werden die entsprechenden Sulfine 4 erhalten. Die Eigenschaften von 4 werden beschrieben.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810823
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  • 5
    Electronic Resource
    Electronic Resource
    Chemie reaktiver Kationen von Schwefeldioxidanalogen, XII. Stereochemie der Heterometathesereaktion mit cyclischen Sulfoxiden  -  Turnstile-Rotation in den intermediären σ-Sulfuranen (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 72-77 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemistry of Reactive Cations Derived from Sulfur Dioxide Analogues, XII.  -  Stereochemistry of the Heterometathesis with Cyclic Sulfoxides  -  Turnstile Rotation in the Intermediate σ-SulfuranesIn the heterometathesis of cyclic sulfoxides with N-Methyl-N-sulfinylmethanaminium tetrafluoroborate (1a), both diastereomers yield the same product, in each case, the reactions proceed with retention or inversion, respectively. This behavior is explained by turnstile rotations in the intermediate σ-sulfuranes, the most stable form of which are observed in the NMR spectra.
    Notes: Bei der Heterometathesereaktion cyclischer Sulfoxide mit N-Methyl-N-sulfinylmethanaminium-tetrafluoroborat (1a) geben jeweils beide Diastereomere dasselbe Produkt - unter Retention bzw. Inversion der Konfiguration. Zur Erklärung wird Turnstile-Rotation in den σ-Sulfuran-Zwischenprodukten zur stabilsten (im NMR-Spektrum nachweisbaren) Form angenommen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850109
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  • 6
    Electronic Resource
    Electronic Resource
    Photolysis of enol acetates and α-bromo derivatives of o-(acyloxy)acetophenones (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 589-598 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Photolyse von Enolacetaten und α-Bromderivaten von o-(Acyloxy)acetophenonenUV-Bestrahlung der Enolacetate 3a - g in Benzol liefert o-(Acetoxy)acetophenone 2 und 2-Methyl-chromone 4 als Hauptprodukte. Unter den gleichen experimentellen Bedingungen bleiben die Dimethylderivate 3h und 3i unverändert. Das α-Bromketon 5a liefert in Abhängigkeit von den Bestrahlungsbedingungen Mischungen aus o-(Acetoxy)acetophenon (2a), dem Diketon 6 und/oder α-Acetoxy-o-hydroxyacetophenon (7). Die Ähnlichkeiten und Unterschiede zwischen beiden Reihen von Experimenten sowie mechanistische Überlegungen werden diskutiert.
    Notes: UV irradiation of enol acetates 3a - g in benzene gives mainly o-(acetoxy)acetophenones 2 and 2-methylchromones 4. Under the same conditions, the dimethyl derivatives 3h and 3i remain unaffected. The α-bromo ketone 5a gives rise to mixtures of o-(acetoxy)acetophenone (2a), the diketone 6, and/or α-acetoxy-o-hydroxyacetophenone (7), depending on the irradiation conditions. The similarities and differences between the two series of experiments, as well as their possible mechanistic implications, are discussed.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850320
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  • 7
    Electronic Resource
    Electronic Resource
    Chemie reaktiver Kationen von Schwefeldioxidanalogen, VI. N-Alkyl-N-sulfinylalkanaminiumsalze  -  Umsetzungen mit Sulfinylverbindungen (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 723-728 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemistry of Reactive Cations Derived from Sulfur Dioxide Analogues, VI1).  -  N-Alkyl-N-sulfinylalkanaminium Salts  -  Reactions with Sulfinyl CompoundsN-Sulfinylalkanaminium salts 1 react smoothly with sulfinyl compounds 2 to give aminosulfonium salts 3. By 1H-NMR spectroscopy an intermediate can be detected which is thought to have a four-membered sulfurane ring structure.
    Notes: N-Sulfinylalkanamininiumsalze 1 reagieren glatt mit Sulfinylverbindungen 2 unter Bildung von Aminosulfoniumsalzen 3. 1H-NMR-spektroskopisch kann ein Zwischenprodukt nachgewiesen werden, dem eine Vierringsulfuranstruktur zugeschrieben wird.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820412
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