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  • 1
    Electronic Resource
    Electronic Resource
    Substituenten-Einfluß auf die lichtinduzierte Isomerisierung des Homofulven-Systems: Photo-Isomerisierung des Singulettangeregten 1,2,3,5-Tetramethyl-4-methylen-endo- und-exo-6-(trifluormethyl)bicyclo[3.1.0]hex-2-ens (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 2681-2691 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Influence of Substituents on the Light-Induced Isomerization of the Homofulvene System: Photo-Isomerization of the Singlet Excited 1,2,3,5-Tetramethyl-4-methylene-endo- and -exo-6-(trifluoromethyl)bicyclo[3.1.0]hex-2-eneSyntheses of the diastereomeric pairs 1,2,3,5-tetramethyl-4-methylene-endo- and -exo-6-(trifluoromethyl)bicyclo[3.1.0]hex-2-ene (endo-1d and exo-1d) as well as [6-D]-endo-1d and [6-D]- exo-1d are reported. Following singlet excitation both diastereomers are isomerized to a mixture of 1,2,3,5-Tetramethyl-6-methylene-endo- and -exo-4-(trifluoromethyl)bicyclo[3.1.0]hex-2-ene (endo-7 and exo-7) as well as [4-D]-endo-7 and [4-D]-exo-7. A mechanism for this - from the singlet excited isomerization of the alkyl-substituted homofulvenes different - reaction path is suggested.
    Notes: Die Synthese der Diastereomeren-Paare 1,2,3,5-Tetramethyl-4-methylen-endo- und -exo-6(trifluormethyl)bicyclo[3.1.0]hex-2-en (endo-1d und exo-1d) bzw. [6-D]-endo-1d und [6-D]-exo-1d wird beschrieben. Die Diastereomeren werden nach Singulett-Anregung übereinstimmend zu einem Gemisch von 1,2,3,5-Tetramethyl-6-methylen-endo- und -exo-4-(trifluormethyl)bicyclo-[3.1.0]hex-2-en (endo- 7 und exo-7) bzw. [4-D]-endo-7 und [4-D]-exo-7 isomerisiert. Ein Mechanismus für diesen - vom Verhalten der alkylsubstituierten Homofulvene stark abweichenden - Reaktionsverlauf wird vorgeschlagen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180711
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  • 2
    Electronic Resource
    Electronic Resource
    Untersuchungen am 6-Deuterio-1,2,3,5-tetramethyl-4-methylen-endo- und -exo-6-(trideuteriomethyl)bicyclo-[3.1.0]hex-2-en über den Mechanismus der Singulett-angeregten Photo-Isomerisierung des Homofulven-Systems (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3551-3559 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: An Investigation of 6-Deuterio-1,2,3,5-tetramethyl-4-methylene-endo- and -exo-6-(trideuteriomethyl)bicyclo[3.1.0]hex-2-ene on the Mechanism of the Singlet Excited Photo-Isomerization of the Homofulvene SystemSyntheses of 6-deuterio-1,2,3,5-tetramethyl-4-methylene-endo- and -exo-6-(trideuteriomethyl)bicyclo[3.1.0]hex-2-ene ([endo-6-CD3, 6-D]-1 and [exo-6-CD3, 6-D]-1) are reported. Following excitation to the S1-state both compounds isomerize to 6-deuterio-1,2,3,4-tetramethyl-5-methylene-6-(trideuteriomethyl)-1,3-cyclohexadiene ([6-CD3, 6-D]-2). The positions of the labelled atoms in 2 are discussed with respect to the mechanism of the photoisomerization 1 → 2.
    Notes: Die Synthesen von 6-Deuterio-1,2,3,5-tetramethyl-4-methylen-endo- und -exo-6-(trideuteriomethyl)bicyclo[3.1.0]hex-2-en ([endo-6-CD3, 6-D]-1 und [exo-6-CD3, 6-D]-1) werden beschrieben. Beide Verbindungen werden nach Anregung in den S1-Zustand zum 6-Deuterio-1,2,3,4-tetramethyl-5-methylen-6-(trideuteriomethyl)-1,3-cyclohexadien ([6-CD3, 6-D]-2) isomerisiert. Aus den Positionen der markierten Atome im Produkt 2 werden Folgerungen über den Mechanismus der Photo-Isomerisierung 1 → 2 abgeleitet.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180911
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  • 3
    Electronic Resource
    Electronic Resource
    Ein Beitrag zum Mechanismus der licht-induzierten Isomerisierungen des 4-Methylenbicyclo[3.1.0]hex-2-en-Systems (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 511-519 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Contribution to the Mechanism of Light-induced Isomerizations of the 4-Methylenebicyclo[3.1.0]hex-2-eneDeuterium-labelling of 1,2,3,5,6-exo-pentamethyl-4-methylenebicyclo[3.1.0]hex-2-ene (exo-1) and 1,2,3,5,6-endo-pentamethyl-4-methylenebicyclo[3.1.0]hex-2-ene (endo-1) was used to get insight into the mechanisms of the reversible photo-isomerization exo-1 ⇌ endo-1 and of their light-induced rearrangements to 1,2,3,4,6-pentamethyl-5-methylene-1,3-cyclohexadiene (2).
    Notes: Durch Verfolgung des Verbleibs von Deuterium im markierten 1,2,3,5,6-exo-Pentamethyl-4-methylenbicyclo[3.1.0]hex-2-en (exo-1) und 1,2,3,5,6-endo-Pentamethyl-4-methylenbicyclo[3.1.0]-hex-2-en (endo-1) wurden Hinweise über die Mechanismen der reversiblen Photo-Isomerisierung exo-1 ⇌ endo-1 und der gleichfalls licht-induzierten Umlagerung dieser Verbindungen zum 1,2,3,4,6-Pentamethyl-5-methylen-1,3-cyclohexadien (2) erhalten.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130209
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  • 4
    Electronic Resource
    Electronic Resource
    Eine Untersuchung an 6-Deuterio-endo- und-exo-6-isopropyl-1,2,3,5-tetramethyl-4-methylenbicyclo[3.1.0]hex-2-en über den Mechanismus der Singulett-angeregten Photo-Isomerisierung des Homofulven-Systems (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 2671-2680 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: An Investigation of 6-Deuterio-endo-and-exo-6-isopropyl-1,2,3,5-tetramethyl-4-methylenebicyclo[3.1.0]hex-2-ene on the Mechanism of the Singlet Excited Photo-Isomerization of the Homofulvene SystemSynthese of the diastereomeric homofulvenes 6-deuterio-endo- and -exo-6-isopropyl-1,2,3,5-tetramethyl-4-methylenebicyclo[3.1.0]hex-2-ene ([6-D]-endo-1 b and [6-D]-exo-1 b) are reported. Following excitation to the S1-state both compounds isomerize to 6-deuterio-6-isopropyl-1,2,3,5-tetramethyl-5-methylene-1,3-cyclohexadiene. A mechanism for the reaction sequence is suggested.
    Notes: Die Synthesen der diastereomeren Homofulvene 6-Deuterio-endo- und -exo-6-isopropyl-1,2,3,5- tetramethyl-4-methylenbicyclo[3.1.0]hex-2-en ([6-D]-endo-1b und [6-D]-exo-1b) werden beschrieben. Beide Verbindungen isomerisieren nach Anregung in den S1-Zustand zu 6-Deuterio-6-isopropyl-1,2,3,4-tetramethyl-5-methylen-1,3-cyclohexadien ([6-D]-2b). Ein Mechanismus für den Verlauf dieser Photo-Isomerisierung wird vorgeschlagen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180710
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