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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1424-1435 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Reaction of 2-Pyrrolecarbaldehyde with Hetero-substituted Ethenes3H-Pyrrolizines 1 have been obtained from reactions of 2-pyrrolecarbaldehyde with ethenylphosphonates 2 and the phosphane oxide 5, respectively, the ratio of products depending on the structure of the educts. On varying the reaction conditions a controlled synthesis of both isomers 1e/f was achieved. Pyrrolizines, formed in a reaction of 2 pyrrolecarbaldehyde with ethenyl phenyl sulfone (3), could not be isolated since the reaction proceeded to give more complex pyrrolizine derivatives and the cyclazine 11. A mechanism is proposed for this multistep reaction. N-Alkylation of 2-pyrrolecarbaldehyde with dihaloalkanes has been carried out using phase transfer catalysis.
    Notes: Umsetzungen des 2-Pyrrolcarbaldehyds mit Ethenylphosphonaten 2 und dem Phosphanoxid 5 führten zu 3H-Pyrrolizinen 1, wobei das Mengenverhältnis der gebildeten Isomeren von der Struktur der Edukte abhängt. In einem Falle (1e/1f) gelang die gezielte Synthese beider Isomeren durch Variation der Reaktionsbedingungen. Die aus 2-Pyrrolcarbaldehyd und Ethenylphenylsulfon (3) entstandenen Pyrrolizine 1e/f reagieren weiter unter Bildung komplexer Pyrrolizinderivate und des Cyclazins 11. Für diese Mehrstufenreaktion wird ein Mechanismus vorgeschlagen. Unter Phasentransfer-Bedingungen gelingen Alkylierungen des 2-Pyrrolcarbaldehyds mit Dihalogenalkanen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 1547-1554 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Multiple-stage Reactions with Participation of Latent α-Hetero-substituted Carbanions: Reaction of 2-Pyrrolecarbaldehyde with 1,2-Disubstituted EthenesThe reaction of 1,2-bishetero-stabilized ethenes 2 with the anion of 2-pyrrolecarbaldehyde (1) yields the pyrrolizine derivatives 4 and 11 or pyrrolo[1′,2′:3,4]pyrimido[2,1,6-cd]pyrrolizines 8. A control of the reaction path and the yields by variation of the substituents of the ethenes 2, the solvent and the reaction temperature may be rationalized using the scheme.
    Notes: Die Umsetzung 1,2-bisheterostabilisierter Ethene 2 mit dem Anion des 2-Pyrrolcarbaldehyds (1) führt zu den Pyrrolizinderivaten 4 und 11 oder den Pyrrolo[1′,2′:3,4]pyrimido[2,1,6-cd]pyrrolizinen 8. Ausbeuten und Reaktionsweg hängen in übersichtlicher Weise (Schema) von den Substituenten der Ethene 2, dem Lösungsmittel und der Reaktionstemperatur ab.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 661-664 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthetic Routes to 1-Substituted ButadienylphosphonatesThe synthesis of 1-substituted butadienylphosphonates 5 was attempted on three routes. The easily polymerizing butadienes are generally accessible from the stable phosphonates 4 by seleninic acid elimination.
    Notes: Die Synthese 1-substituierter Butadienylphosphonate 5 wurde auf drei Wegen versucht. Dabei zeigte sich, daß die polymerisationsfreudigen Butadiene aus den stabilen Phosphonaten 4 durch Seleninsäureeliminierung schnell und bequem zugänglich sind.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 655-659 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Bifunctional Molecules with Acceptor-Substituted ButadienesThe butadienyl sulfone 1 and the chlorobutenyl sulfone 2 react under six-ring annulation with salicylaldehyde to give 4 and with 1-(cyclohexenyl)piperidine to give 7. Reaction with 2-pyrrolecarbaldehyde yields the 3a-azaazulenes 10a-c together with the vinylcyclopent-indolizine 14, formed in a 6-step reaction sequence. The isomeric imidazolecarbaldehydes 15 and 17 react analogously to yield the diazaazulenes 16 and 18, respectively. From a multistep reaction of 2-pyrrolecarbaldehyde and the bisphosphonium salt 20 the pyrrolyl-3a-azaazulene 23a has been obtained.
    Notes: Das Butadienylsulfon 1 und das Chlorbutenylsulfon 2 reagieren unter Sechsring-Anellierung mit Salicylaldehyd zu 4 und mit 1-(Cyclohexenyl)piperidin zu 7. Mit 2-Pyrrolcarbaldehyd entsteht neben den erwarteten 3a-Azaazulenen 10a-c das Vinylcyclopent-indolizin 14 in einer sechsstufigen Reaktionsfolge. Die beiden Imidazolcarbaldehyde 15 und 17 reagieren analog zu den Diazaazulenen 16 und 18. Das Pyrrolyl-3a-azaazulen 23a entsteht in einer Mehrstufenreaktion aus 2-Pyrrolcarbaldehyd und dem Bisphosphoniumsalz 20.
    Type of Medium: Electronic Resource
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