75735-27-2Relevant articles and documents
Nitrile-forming Eliminations from Oxime Ethers
Hegarty, Anthony F.,Tuohey, Patrick J.
, p. 1313 - 1317 (2007/10/02)
The oxime ethers (7) and (8) (R = alkyl or aryl) undergo base-catalysed elimination to benzonitriles (3) in water-dioxan (4 : 1) at 25 deg C.The Z-isomer (8Z) reacts via hydroxide-catalysed antiperiplanar elimination 70-fold more rapidly than the corresponding E-isomer.Electronic effects on syn-elimination (from 7E) show that electron-withdrawing groups aid elimination in both Ar and in the leaving group -OR; no intramolecular assistance is observed in these substrates.These results are interpreted in terms of a central E2 elimination, with appreciable C-H and N-O- bond cleavage in the transition state.