REACTIVITY OF 2-CHLOROCYCLOHEXANONES AND 2-(TOSYLOXY)CYCLOHEXANONES TOWARDS ANIONS ELECTROGENERATED AT CARBONIUM AND NITROGEN-ATOMS - ELECTROCHEMICALLY INDUCED FAVORSKII REARRANGEMENT

Authors
DEANGELIS F FEROCI M INESI A
Citation
F. Deangelis et al., REACTIVITY OF 2-CHLOROCYCLOHEXANONES AND 2-(TOSYLOXY)CYCLOHEXANONES TOWARDS ANIONS ELECTROGENERATED AT CARBONIUM AND NITROGEN-ATOMS - ELECTROCHEMICALLY INDUCED FAVORSKII REARRANGEMENT, Bulletin de la Societe chimique de France, 130(5), 1993, pp. 712-719
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
5
Year of publication
1993
Pages
712 - 719
Database
ISI
SICI code
0037-8968(1993)130:5<712:RO2A2T>2.0.ZU;2-U
Abstract
Carbonium and nitrogen anions were generated by cathodic reduction of 6, 7 and 8 or by deprotonation of 9 and 10 (by means of electrogenerat ed bases). Their reactivity towards alpha-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 me chanisms, respectively. In most cases. the reaction pathway appears to be driven by the applied electric potential. The Favorskii rearrangem ent undergone by 1 and 2 under electrochemical conditions can also be induced by nitrogen (Ph-NH-NBAR-Ph) and carbonium (CH3COCHCO2EtBAR) an ions. which have never been used before in this kind of reaction.