The following double polarization method is suggested as a result of these investigations. Dissolve the normal weight of sample in a ioo cc. flask, clarify with an appropriate amount of lead acetate, make up to volume and filter (the usual procedure for commercial polarizations). Transfer 50 cc. of filtrate to a 100 cc. flask, add 15 cc. of a 20 per cent solution of monochloroacetic acid, make up to volume with water, and polarize within 15 min. after adding the acid.To invert, transfer about 50 cc. of the solution to a 50 cc. flask, stopper tightly by tying down the cork,
UNSATURATED FATTY ACIDS OF FISH OILS 1289 tetraphenyl-succinonitrile. Each of these substances was identified by its melting point and the melting point of a mixture with samples of known structure.
Benzoyl-phenyl-nitrocyclopropaneFive and three-tenths g. of the cyclopropane derivative was reduced in 50 cc. of methyl alcohol in the presence of 0.25 g. of platinum black. The reduction was stopped when 740 cc. of hydrogen had been absorbed. The platinum was removed after boiling the suspension to redissolvc a white solid which had separated during the reduction. On cooling the clear solution, it deposited 1.9 g. of a colorless solid which crystallized in needles and melted at 98-99°. A mixed melting point showed that this was /3-phenyl-7-nitro-butyrophenone. Summary 1. This paper gives an account of the results obtained by reducing a series of ,ß-unsaturated nitro compounds with hydrogen and platinum.2. In a discussion of the results it is shown that the behavior of ,ßunsaturated nitro compounds on catalytic reduction is essentially the same as that of ,/3-unsaturated ketones. The resulting saturated nitro compounds, however, generally undergo further reduction; the successive steps are RCH: CHN02 -> RCH2CH2N02 -[RCH2CH2NO] -RCH2CH: NOH -> RCH2CH: NH -> RCH2CH2NH2.3. The primary reduction product of a cyclopropane derivative which has a nitro group in direct union with one of the ring carbon atoms is likewise a saturated nitro compound.Cambridge 38, Massachusetts
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