Oximes Beckmann rearrangement

Keywords oxime, Beckmann rearrangement, nitrile ylide, amide... 

Wittig reaction, 151 —, cyanohydrin, 149, 324 —, ketal, bromination, 168 —, oxime, Beckmann rearrangement, 343... 

The Mexican owners of Syntex recruited after Marker s departure George Rosenkranz. Within two years, Rosenkranz succeeded not only in the large-scale production of progesterone, but he also estabhshed the synthesis of the male sex hormone, testosterone, from yam roots. The synthesis starts from 16-dehydro-pregnenolone acetate, which is converted into its oxime Beckmann rearrangement ofthe latter is followed by hydrolysis and yields 5-androsten-3)3-ol-17-one acetate. 

Nylon 6 is produced from caprolactam. Phenol is hydrogenated to cyclo-hexanol. This cyclohexanol is dehydrogenated to cyclohexanone, which is then converted to its oxime. Beckmann rearrangement of the oxime gives caprolactam, which is largely converted to a linear polymer on heating underpressure (Eqs. 30-31)-... 

ORAC, there are literature precedents for conversion of a ketone to an oxime, Beckmann rearrangement of oximes and for hydrolysis of amides, but no such composite reactions. This simple example highhghts a general problem of searching reaction databases the need to be able to find sequences of reactions that satisfy a user s query, when necessary. 

---