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  • 1
    Electronic Resource
    Electronic Resource
    Pentacarbonylchrom-Komplexe von 1H-Isoindolen (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 1919-1930 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Pentacarbonylchromium Complexes of 1H-IsoindolesThe 1H-isoindoles 1e-k are converted into the pentacarbonylchromium complexes 4e-k by means of ligand exchange reactions with pentacarbonyl(η2-cis-cyclooctene)chromium (3). Likewise, the 2H-isoindoles (2a-d) which are able to undergo tautomerism are complexed in the 1H-form 4a-d. This reaction allows, for the first time, to isolate even unsubstituted 1H-isoindole (1a) from the equilibrium with 2H-isoindole (2a) as a stable derivative 4a. The structure 4 of the pentacarbonyl(η1-1H-isoindole)chromium complexes is elucidated from the analytical and spectroscopic data (IR, 1H and 13C NMR, MS) as confirmed by means of an X-ray structure analysis of the 3-ethoxy-1H-isoindole complex 4e.
    Notes: Die 1H-Isoindole 1e-k werden durch Ligandenaustausch mit Pentacarbonyl(η2-cis-cycloocten)chrom (3) in die Pentacarbonylchrom-Komplexe 4e-k übergeführt; tautomeriefähige 2H-Isoindol (2a-d) werden ebenfalls in der 1H-Form komplexiert (4a-d). Diese Reaktion erlaubt erstmals, auch das unsubstituierte 1H-Isoindol (1a) aus dem Gleichgewicht mit 2H-Isoindol (2a) in Form eines stabilen Derivats 4a zu isolieren. Die Struktur 4 der Pentacarbonyl(η1-1H-isoindol)chrom-Komplexe ergibt sich aus den analytischen und spektroskopischen Daten (IR, 1H- und 13C-NMR, MS) und wird durch eine Röntgenstrukturanalyse des 3-Ethoxy-1H-isoindol-Komplexes 4e bestätigt.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190614
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  • 2
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXIV. 2-tert-Butyl-2H-isoindol - Substitutionsreaktionen mit Elektrophilen (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 337-342 
    Details
    ISSN: 0009-2940
    Keywords: Isoindoles ; Substitution with electrophiles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Chemistry of Isoindoles and Isoindolenines, XXXIV. - 2-tert-Butyl-2H-isoindole - Substitution Reactions with ElectrophilesThe thermally remarkable stable o-quinonoid hetarene 2 reacts with electrophiles in α-position to the heteroatom and can be protonated and alkylated. The reactions with arenediazonium tetrafluoroborates lead to the formation of the substitution products 10.
    Notes: Das thermisch bemerkenswert stabile o-chinoide Hetaren 2 reagiert mit Elektrophilen in α-Stellung zum Heteroatom und ist protonierbar und alkylierbar. Bei Reaktionen mit Arendiazonium-tetrafluoroboraten entstehen die Substitutionsprodukte 10.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220222
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  • 3
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVI1. Reaktionen von 2-Alkyl-2H-isoindolen mit Maleinimiden (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 381-390 
    Details
    ISSN: 0009-2940
    Keywords: o-Quinoid hetarenes / Isoindoles, cycloaddition reactions with / Dienophiles, CC ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVI - Reactions of 2-Alkyl-2H-isoindoles with Maleic Imides2-Alkyl-2H-isoindoles 2 react with maleic imides 4 exclusively in position 1 and 3 by cycloaddition to form Diels-Alder adducts. The transformation of the endo isomers 6 into the thermodynamically more stable exo isomers 7 depends on the dienophile. The cycloaddition is useful for analytical detection of o-quinoid hetarenes 2 and for the synthesis of 7-azabicyclo[2.2.1]heptenes.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230225
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  • 4
    Electronic Resource
    Electronic Resource
    Heterocyclen mit einem Azaallyl-System, 4. 5H-Dibenz[c,e]azepine mit Donor-Gruppen in 7-Stellung (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2085-2090 
    Details
    ISSN: 0009-2940
    Keywords: 5H-Dibenz[c,e]azepines ; Imidates ; alkyl ; heterocyclic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Heterocycles with an Azaallyl System, 4.  -  5H-Dibenz[c,e]azepines with Donor Groups at the 7-Position5H-Dibenz[c,e]azepines substituted with a methoxy (1) or methylthio group (10) at the 7-position have been synthesized from 6,7-dihydro-5H-dibenz[c,e]azepin-5-one (5) by regioselective O- or S-alkylation with methyl trifluoromethansulfonate and subsequent NH-deprotonation. According to the spectroscopic properties the semicyclic 7-membered alkyl imidates exist exclusively in the benzenoid 5H structure.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240934
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  • 5
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXIX. Reaktionen von 2-Alkyl-4,5,6,7-Rn-2H-isoindolen (Rn=tetramethyl, tetrachlor) mit aktivierten C=C-Dienophilen (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 183-189 
    Details
    ISSN: 0009-2940
    Keywords: 2H-Isoindoles, 2-alkyl-, reactions with C=C dienophiles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on the Chemistry of Isoindoles and Isoindolenines, XXXIX.  -  Reactions of 2-Alkyl-4,5,6,7-Rn-2H-isoindoles (Rn=tetramethyl, tetrachloro) with Activated C=C DienophilesSubstituted 2H-Isoindoles 2 react with maleic imides in absolute ether. Cycloaddition in 1,3-position leads to the formation of 1:1 adducts. The ratio between endo isomers 4 and exo isomers 5 depends on the substituents and the solvents. In the case of steric hindrance the Diels-Alder addition can be induced by Lewis acids. In the presence of oxygen-substituted 4,5,6,7-tetrachloro-2-methylisoindolin-1-ones 7 are formed as minor products.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250130
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  • 6
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVII. Symmetrisch substituierte 2-Alkyl-2H-isoindole (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1719-1727 
    Details
    ISSN: 0009-2940
    Keywords: Isoindoles, symmetrically substituted ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVII1) - Symmetrically Substituted 2-Alkyl-2H-isoindoles2-Alkyl-Rn-2H-isoindoles (1; Rn=4,5,6,7-tetramethyl, 4,5,6,7-tetrachloro) have been prepared efficiently by the N-oxide route and characterized by spectroscopic means.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230823
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  • 7
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXIX. Reaktionen des 2H-Isoindols mit Maleinimiden: Ein einfaches Herstellungsverfahren für 7-Azabicyclo[2.2.1]heptene (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 927-934 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Chemistry of Isoindoles and Isoindolenines, XXIX.  -  Reactions of 2H-Isoindole with Maleic Imides: A Simple Procedure for the Preparation of 7-Azabicyclo [2.2.1]heptenesSolutions of 2H-isoindole 1 in ether were prepared by a simple procedure and treated with maleic imides 2. 1,3-Cycloaddition reactions lead to the formation of 1:1 adducts 3 with an 7-azabicyclo[2.2.1]heptene frame. The endo isomers 3.1 can thermally be isomerized to the more stable exo isomers 3.2. The constitution and configuration of the 1:1 cycloadducts 3 are established by 1H- and 13C-NMR spectroscopy.
    Notes: Lösungen des 2H-Isoindols 1 in Ether werden nach einem einfachen Verfahren hergestellt und mit Maleinimiden 2 umgesetzt. 1,3-Cycloadditionsreaktionen führen zu 1:1-Addukten 3 mit der Struktur von 7-Azabicyclo[2.2.1]heptenen. Die endo-Isomeren 3.1 lassen sich thermisch in die stabileren exo-Isomeren 3.2 umlagern. Konstitution und Konfiguration der 1:1-Cycloaddukte 3 werden durch die 1H- und 13C-NMR-Spektren begründet.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210517
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  • 8
    Electronic Resource
    Electronic Resource
    2,3-Dihydro-2,3-bismethylenbenzo[b]thiophen, ein anelliertes reaktives Dien (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 1203-1205 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,3-Dihydro-2,3-bismethylenebenzo[b]thiophene, a Reactive Annellated DieneThe cis configurated annellated diene 4 is generated in solution by the reaction of the easily accessible 2,3-bis(bromomethyl)-benzo[b]thiophene (3) with sodium iodide. In the presence of CC or NN dienophiles [4+2] cycloaddition reaction take place and lead to 5, 6, 11, and 12 with acceptable yields. This annellation method is useful for the synthesis of polycyclic compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210629
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  • 9
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXI. 4,5,6,7-Tetrachlor- und 4,5,6,7-Tetrabrom-2H-isoindol (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 1827-1832 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Chemistry of Isoindoles and Isoindolenines, XXXI. 4,5,6,7-Tetrachloro- and 4,5,6,7-Tetrabromo-2H-isoindolesThe crystalline 2H-isoindoles 4b are synthesized starting with substituted 2-methylsulfonyl-2,3-dihydro-1H-isoindoles 3 by base-induced elimination of methanesulfinic acid. Compared with the parent compound, a considerable thermal stabilization and chemical deactivation is caused by the halogen atoms at the carbocyclic system. The spectroscopic properties of the o-quinonoid hetarenes 4b have been investigated.
    Notes: Die kristallinen 2H-Isoindole 4b werden aus substituierten 2-Methylsulfonyl-2,3-dihydro-1H-isoindolen 3 durch Basen-induzierte Eliminierung von Methansulfinsäure synthetisiert. Die Halogenatome am carbocyclischen System bewirken - verglichen mit dem Grundkörper - eine beträchtliche thermische Stabilisierung und chemische Desaktivierung. Die spektroskopischen Eigenschaften der o-chinoiden Hetarene 4b wurden untersucht.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881211022
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  • 10
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXVII. 2-Alkyl-2H-dibenz[e,g]isoindole: Synthese, Eigenschaften, Reaktionen (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 81-87 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Chemistry of Isoindoles and Isoindolenines, XXVII. - 2-Alkyl-2H-dibenz[e,g]isoindoles; Synthesis, Properties, ReactionsThe tetracyclic hetarenes 6 are easily accessible via the N-oxide route starting with 9,10-bis(bromomethyl)phenanthrene (3) in a three-step procedure. The twofold annelation reduces the diene reactivity of the central 2H-isoindole system. Cycloaddition occurs as well with activated alkynes as with arynes. The hetarenes 6 can be protonated with trifluoroacetic acid and substituted by reaction with arenediazonium tetrafluoroborates.
    Notes: Die tetracyclischen Hetarene 6 sind nach dem N-Oxid-Verfahren einfach aus 9,10-Bis(brommethyl)phenanthren (3) präparativ dreistufig zugänglich. Durch die zweifache Anellierung wird die Reaktivität des zentralen 2H-Isoindol-Systems abgeschwächt. Cycloaddition tritt sowohl mit aktivierten Alkinen als auch mit Arinen ein. Die Hetarene 6 sind mit Trifluoressigsäure protonierbar und durch SE-Reaktion mit Arendiazonium-tetrafluoroboraten substituierbar.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210113
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