The Reactions of Aldoxime Derivatives with Bases. II. The Reactions of Carbethoxy-α-benzaldoximes with Sodium Hydroxide

The Preparation of Nitriles.

“…to give nitriles (250). In general, the oxime carbonates give higher yields of nitriles than the acetates (251). Studies of the action of benzoyl chloride on syn-and anti'-oximes have led to the conclusion that an equilibrium exists under basic conditions between the syn-and anti-benzoates.…”

Ammonolysis in Liquid Ammonia.

“…Carbethoxy-a-benzaldoximes react similarly (113) (see table 4). TABLE 4 Products obtained in the action of carbethoxy-a-benzaldoximes with potassium amide in liquid ammonia After heating acetophenone with twice its volume of liquid ammonia (at 180°C.…”

ACYLATION OF ALDOXIMES. III. THE CONFIGURATION OF DIPHENYLCARBAMYL AND PICRYL ETHER DERIVATIVES PREPARED FROM syn ALDOXIMES1

“…Although acetyl syn aldoximes with hot alkali undergo mainly hydrolysis giving syn aldoxime, this is not so with certain other acyl syn derivatives. Thus, carbethoxy syn aldoximes with hot alkali give considerable or even largely nitrile (4). There is little doubt that these carbethoxy derivatives have the syn configuration, since (similar to acetyl syn aldoximes) they give practically entirely the corresponding syn aldoxime (4) with cold alkali.…”

“…Thus, carbethoxy syn aldoximes with hot alkali give considerable or even largely nitrile (4). There is little doubt that these carbethoxy derivatives have the syn configuration, since (similar to acetyl syn aldoximes) they give practically entirely the corresponding syn aldoxime (4) with cold alkali. The fact that a carbethoxy syn derivative with hot alkali gives a higher yield of nitrile, and a correspondingly lower yield of syn aldoxime, than the analogous acetyl syn aldoxime is explained on the basis that the former undergoes hydrolysis less readily, and/or the elimination reaction, more readily than the acetyl derivative.…”