Djerassi, Carl's team published research in Journal of the American Chemical Society in 82

Djerassi, Carl published the artcileOptical rotatory dispersion studies. XLIII. Absolute configurational assignment of α-substituted carboxylic acids by anomalous rotatory dispersion of their acylthiourea derivatives, Recommanded Product: Morpholine-4-carbothioamide, the publication is Journal of the American Chemical Society (1960), 5755-6, database is CAplus.

cf. CA 54, 7574h; 55, 7476f. In order to show anomalous rotatory dispersion, carboxylic acids must be converted to derivatives containing a chromophore. The acyl thioureas, RCONHCSNR’₂, were suitable, especially when NR’₂ = morpholino; they showed pos. Cotton effects when R belonged to the L series, neg. when R was D. In a typical preparation, the acid chloride from 120 mg. dehydroabietic acid and excess SOCl₂ was refluxed 1 hr. with 44 mg. KSCN in 4 cc. Me₂CO. Morpholine (0.6 cc.) was added, heating continued 10 min., and the mixture kept overnight. Removal of solvent, addition of H₂O and dilute acid, and extraction with Et₂O yielded 86% dehydroabietyl morpholinothiocarbamide, m. 102-4° (hexane), λ (MeOH) 282 and 340 mμ, log ε 4.16 and 2.41. This derivative showed a pos. Cotton effect, while that of acetoxypodocarpic acid showed a neg. one; the 2 substances differed stereochem. only in configuration at the center adjacent to the CO₂H.

Journal of the American Chemical Society published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Recommanded Product: Morpholine-4-carbothioamide.

Referemce:
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