Lactones in Liquid Ammonia

Glattfeld, J. W. E.; Macmillan, Duncan

doi:10.1021/ja01297a014

Cited by 8 publications

(8 citation statements)

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“…Such studies have also been extended to the ammonolysis of desmotroposantonin 246). The available evidence confirms Glattfeld's statement (98) that in contrast to simple esters lactones are never partially ammonolyzed. They are either completely ammonolyzed or not ammonolyzed at all.…”

Section: Lactonessupporting

confidence: 69%

“…Coumarin and the lactone of 7-hydroxybutyric acid are not affected by liquid ammonia at its boiling point, although the latter is ammonolyzed at room temperature in a sealed tube. Later work (98) confirmed the results on cZ-glucono-7-lactone and coumarin and demonstrated the complete ammonolysis of 3-benzalphthalide (amide of desoxybenzoincarbonic acid).…”

Section: Lactonessupporting

confidence: 54%

“…More recently Glattfeld and Macmillan (98) have shown that butyl acetate, ethyl benzoate, methyl salicylate, and glycerol monoacetate are not ammonolyzed (-33°C. ), while methyl, ethyl, propyl, and butyl lactates, ethyl mandelate, and ethyl phenylacetate are ammonolyzed (30 to 50 per cent in the case of the lactates).…”

Section: Esters Of Carboxylic Acidsmentioning

confidence: 99%

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Ammonolysis in Liquid Ammonia.

Fernelius¹,

Bowman²

1940

Chem. Rev.

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Section: Lactonessupporting

confidence: 69%

Section: Lactonessupporting

confidence: 54%

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Ammonolysis in Liquid Ammonia.

Fernelius¹,

Bowman²

1940

Chem. Rev.

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“…Glattfeld and Macmillan (72) have investigated the reactions between liquid ammonia at its boiling point and certain lactones and esters. Of the lactones studied, only d-glucono-y-lactone and 3-benzalphthalide were ammonolyzed.…”

Section: Nh3mentioning

confidence: 99%

“…The ammonolysis of a number of acetone compounds of a-hydroxy acids has been found to result in the formation of the corresponding acid amides (72). The best yields, amounting to 85-90 per cent., were obtained by treating the compounds with liquid ammonia at room temperature.…”

Section: Nh3mentioning

confidence: 99%

Liquid ammonia research in 1936—A review

Cappel¹,

Watt²

1937

J. Chem. Educ.

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P ROBABLY no single phase of research concerned with liquid ammonia solutions has contributed more to fundamental chemical theory than studies on the nature of solutions of metals.Over a period of years, Professor C. A. Kraus and his students have provided extensive experimental data relative to the nature of such solutions. Largely from these studies there have been developed the basic theories which are now generally used to interpret the physical and chemical properties exhibited by these solutions.Briefly, it is believed that a solution of an alkali metal, M, in liquid ammonia, contains positively charged metal ions and negative electrons. Depending upon the concentra&on, the electrons may be relatively free, or associated with molecules of the solvent ammonia M 4 M t + e -, e-+ nNHa + e-(NHJ.Since the evidence in support of this view has been adequately treated in reviews appearing in THrs JOURNAL (1, 2) and elsewhere (3, 4), it is sufficient for present that both the sodium ion and the ammonium group are ammonated. Aside from the relative merits of differing interpretations of a given set of experimental data, it should be kept in mind that the ultimate clarification of any controversial question is often advanced by the appearance of views not entirely in accord with otherwise generally accepted theories. Particularly is this true when it causes a revival of interest and thereby results in new evidence being brought forth, or in stimulating a more complete utilization of available data.A method for the determination of the density of solutions of salts in liquid ammonia has been described by Johnson and Martens (8). They have measured the densities of solutions of the chlorides, bromides, and iodides of lithium, sodium, and potassium at temperatures ranging from -32' to -60°C., and over as wide a range of concentration as permitted by the solubility of the salts. In each case, the density was found to be a linear function of the temperature, and a t lower concentrations, apparently a linear function of the mole fraction of dissolved salt. From the density data for ~otassium iodide it has been shown that a near purposes to again emphasize the fact that a wide variety linear reiationship exists between the apparent molal of experimentally observed phenomena may be satis-volume of the solute and the square root of the concenfactorily explained on this basis. tration expressed in moles per liter of solution. This An alternative explanation of the nature of systems empirical generalization has previously been shown to consisting of alkali metals in liquid ammonia has re-apply to many aqueous salt solutions. ~h~ molar e n f l y been proposed (5). The idea has been advanced heats of solution of ammonium chloride, ammonium that the alkali metals exist in ammonia, not as ions, but bromide, lead iodide, mercuric iodide, lithium bromide, rather as colloidal particles, a view which was 6rst ad-lithium iodide, rubidium bromide, absolute ethyl alvanced by Ostwald (6). Hence, this theory also denies cohol, and pyridine i...

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