Lactams oximes, cyclic, ring

Thionyl chloride Beckmann rearrangement Lactams from cyclic oximes Ring expansion... 

Ethylenenitriles and lactams from cyclic oximes—Ethylenenitriles from lactams—Ring opening and expansion s. 11, 549... 

Poly phosphoric acid sodium azide Lactams from cyclic ketones by Schmidt reaction and from cyclic oximes by Beckmann rearrangement Ring expansion... 

The reaction with oximes of cyclic ketones leads to formation of lactams (e.g. 6 — 7) by ring enlargement ... 

The Beckmann rearrangement of cyclic oximes results in lactams. This is exemplified in Figure 11.38 with the generation of e-caprolactam, the monomer of nylon-6. The nitrilium ion intermediate cannot adopt the preferred linear structure because it is embedded in a seven-membered ring. Therefore, in this case the intermediate might better be described as the resonance hybride of the resonance forms A (C=N+ triple bond) and B (C+=N double bond). The C,N multiple bond in this intermediate resembles the bond between the two C atoms in benzyne that do not carry H atoms. 

HCl-HOAc-AcjO, POCls, BiCla, neat with FeCls, and polyphosphoric acid. The reaction has been done in supercritical water and in ionic liquids. A polymer-bound Beckman rearrangement has been reported. Sim-ply heating the oxime of benzophenone neat leads to A-phenyl benzamide. The oximes of cyclic ketones give ring enlargement and form the lactam,as in the formation of caprolactam (83) from the oxime of cyclohexanone. Heating an... 

The anti group is the one that migrates in this reaction. If the reaction is performed on an oxime of a cyclic ketone, then ring enlargement occurs and gives the corresponding lactam. 

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