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SummaryA new, economic technique was developed for the production of 2-alkyl-2-oxazolines with saturated, unsaturated or OH-functionalized alkylrests. In the process the fatty acids are changed into polymerizable monomers.The cationic polymerization of fattyalkyl-2-oxazolines was investigated in unpolar solvents and in bulk. It reacts in a living mechanism. The polymerization is remarkable inert against impurities like water or ethanolamide. A reaction enthalpy o f d H = 85,9 kJ/mol was found for the bulk polymerization of 2-pentadecyl-2-oxazoline. ZusammenfassungEs wurde ein neues, wirtschaftliches Verfahren zur Herstellung von 2-Alkyl-2-oxazolinen mit gesattigten, ungesattigten und OH-funktionellen Alkylresten entwickelt, durch das Fettsauren in polymerisierbare Monomere umgewandelt werden konnen.Die kationische Polymerisation der Fettalkyloxazoline wurde in unpolaren Losungsmitteln und in Substanz untersucht. Sie verlauft nach einem lebenden Mechanismus. Die Polymerisation ist gegen Verunreinigungen wie Wasser oder Ethanolamid bemerkenswert inert. Fiir die Substanzpolymerisation von 2-Pentadecyl-2-oxazolin wurde die Reaktionsenthalpie A H mit 85,9 kJ/mol bestimmt.

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fraction (ft) of unconverted 1 at time t was determined from the IR spectra by using the ratio of the intensity of the absorption band at 5.7 µ , which is due to the carbonyl band for 1, to the intensity of the absorption band at 6.2 µ , which is an aromatic band found in all samples and, consequently, remains relatively constant. The decrease in ft as a function of t is first order as shown in Figure 1, from which was deduced that the half-life of 1 under these conditions is about 90 h.The NMR spectra of the samples, removed after 8,76, and 296 h, showed that the components of the mixture were 1, 5, and 4 and that the corresponding ratio changed from 90:9:1 after 8 h to 6:3:1 after 76 h to 2:9:9 after 296 h. (b) With NH3 Vapor Saturated with H20 To Give 4 (Expt 15). Experiment 14 was repeated with the modification that air was metered into the system after it was bubbled through concentrated aqueous NH4OH (i.e., 30% NH3). Samples were removed after 1.5, 3, 5, 6.5, and 22 h. The data (Figure 1) show 100% conversion to 5 showing that little or no side products are formed in the conversion.

The /3-lactamase inactivator 6-(methoxymethylene) penicillanic acid is the first compound in a new class of penams having a heteroatom-substituted methylene group at the 6-position conjugated to the /3-lactam carbonyl.Treatment of benzyl 6-oxopenicillanate with the anion of methoxy(trimethylsilyl)methane gives a pair of /3-silyl alcohols. Quantitative acetylation of either of the alcohols and subsequent fluoride-promoted elimination of acetate and trimethylsilyl fluoride yields an equilibrium mixture of the Z and E isomers of the title compound.