126587-31-3Relevant articles and documents
Gas-phase Rearrangements of Deprotonated Ketoximes, Ketoxime Ethers, and Aldoximes. A Negative-ion Beckmann Rearrangement
Adams, Gregory W.,Bowie, John H.,Hayes, Roger N.
, p. 2159 - 2168 (2007/10/02)
Evidence is presented which indicates that the pronounced loss of water from deprotonated ketoximes involves specific proton transfer followed by a negative-ion Beckmann rearrangenment.For example, Me2C=NO- -> -CH2(Me)C=NOH -OH> -> CH2=C=NCH2- + H2O.Deprotonated aldoximes, e.g.MeCH=NO-, fragment in this way, but also undergo the competing process MeCH=NO- -> MeC=NOH -> -OH> -> -CH2CN + H2O.Other rearrangements occur when proton transfer to oxygen does not occur; e.g.Ph2C=NO- PhC=NOPh -> PhO- + PhCN.