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4-Phosphoranylidene-5(4H)-oxazolones II. Reactions with alkylating agents

4-Phosphoranyliden-5(4H)-oxazolone, 2. Mitt. Reaktionen mit Alkylierungsreagentien

  • Organische Chemie Und Biochemie
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Summary

When treated with alkyl halides at 20–90°C without solvent or in acetonitrile, 4-phosphoranylidene-5(4H)-oxazolones (1) give 4-C-alkylation products4 in good yields. Alkylation of1 with alkyl triflates in CH2Cl2 at room temperature results in O-alkylation products5. No O-to 4-C-alkylation rearrangement can be observed. The spectroscopic properties of the alkylation products are reported and discussed.

Zusammenfassung

Behandlung von 4-Phosphoranyliden-5(4H)-oxazolonen (1) mit Alkylhalogeniden bei 20–90°C ohne Lösungsmittel oder in Acetonitril liefert in guten Ausbeuten die 4-C-alkylierten Produkte4. Alkylierung von1 mit Alkyltriflaten in CH2Cl2 bei Raumtemperatur ergibt O-alkylierte Produkte (5). E6 wurde keine Umlagerung von O-alkylierten zu C-alkylierten Verbindungen beobachtet. Die spektroskopischen Eigenschaften der Alkylierungsprodukte werden berichtet und diskutiert.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Silesian Technical University, PL-44100, Gliwice, Poland

    R. Mazurkiewicz & A. W. Pierwocha

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  1. R. Mazurkiewicz
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  2. A. W. Pierwocha
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Mazurkiewicz, R., Pierwocha, A.W. 4-Phosphoranylidene-5(4H)-oxazolones II. Reactions with alkylating agents. Monatsh Chem 128, 893–900 (1997). https://doi.org/10.1007/BF00807098

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  • DOI: https://doi.org/10.1007/BF00807098

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