13618-30-9Relevant articles and documents
Reactivity of 2-chloro- and 2-(tosyloxy)cyclohexanones towards anions electrogenerated at carbonium and nitrogen atoms. Electrochemically induced Favorskii rearrangement
Angelis, F. De,Feroci M.,Inesi, A.
, p. 712 - 719 (2007/10/02)
Carbonium and nitrogen anions were generated by cathodic reduction of 6, 7 and 8 or by deprotonation of 9 and 10 (by means of electrogenerated bases).Their reactivity towards α-substituted ketones 1 and 2 was studied.The reaction products 5b-d, 4b and 3 are formed according to the Favorskii rearrangement, substitution, and formal reduction mechanisms, respectively.In most cases, the reaction pathway appears to be driven by the applied electric potential.The Favorskii rearrangement undergone by 1 and 2 under electrochemical conditions can also be induced by nitrogen (Ph-NH--Ph) and carbonium (CH3COC-HCO2Et) anions, which have never been used before in this kind of reaction. - Keywords: probase / Favorskii rearrangement / electrogenerated anions / α-substituted cyclohexanones