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The rhodium catalysed hydroaminomethylation of the unsaturated fatty acid derivatives oleic acid ethyl ester (1) and oleyl alcohol (2) with the primary amines hexylamine (3), benzylamine (4), aspartic acid diethyl ester (5) and valinol (6), and with the secondary amine morpholine (7), respectively, proceeds with good to excellent yields. Using primary amines the structure of the reaction products depends on the stoichiometry of the reactants. Performing the reaction of (1) with (3) with an excess of the amine compound the corresponding secondary amine (9) (1:1-adduct) was observed. Working with a 2-fold excess of (1) the tertiary amine (16) (2:1-adduct) was the main product.

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NotesVol. 75 tion with acetic anhydride gave the acetyl derivative, m.p. 207-210°, no depression on mixed melting point with an authentic specimen of acetylpodophyllotoxin. Treatment with piperidine in boiling alcohol (footnote 4, procedure for epipicropodophyllin) gave picropodophyllin (m.p. 213-223°) in 75% yield; acetyl derivative, m.p. 211-214°, no mixed m.p. depression with an authentic specimen of acetylpicropodophyllin. The ultraviolet and infrared absorption spectra were identical with those of podophyllotoxin from podophyllin.5Savinin.-Fractions D, E and F were combined (0.12% yield) and crystallized first from benzene then from absolute ethanol, yielding large, colorless, transparent prisms m.p. 146.4-148.4°, [<*]2'd -87°( c 0.95, chloroform).

The rhodium catalysed hydroaminomethylation of the unsaturated fatty acid derivatives oleic acid ethyl ester (1) and oleyl alcohol (2) with the primary amines hexylamine (3), benzylamine (4), aspartic acid diethyl ester (5) and valinol (6), and with the secondary amine morpholine (7), respectively, proceeds with good to excellent yields. Using primary amines the structure of the reaction products depends on the stoichiometry of the reactants. Performing the reaction of (1) with (3) with an excess of the amine compound the corresponding secondary amine (9) (1:1-adduct) was observed. Working with a 2-fold excess of (1) the tertiary amine (16) (2:1-adduct) was the main product.

SummaryFourteen petroleum ether‐soluble and 16 insoluble DNPH derivatives have been isolated from rancid corn oil and their properties discussed. Evidence suggests that n‐undecanal and n‐undecenal are among the components of the rancid oil.

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