Journal of the Chemical Society. Perkin transactions II p. 1313 - 1317 (1980)
Update date:2022-08-05
Topics: Workup Elimination Reaction Oxime Ether Formation Activation of Oxime Ether
Hegarty, Anthony F.
Tuohey, Patrick J.
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.
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Doi:10.1016/S0040-4039(00)77425-9
(1980)Doi:10.1002/kin.20811
(2013)Doi:10.1039/jr9610003448
(1961)Doi:10.1007/BF00903317
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(1981)Doi:10.1021/ja01490a062
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