170307-14-9Relevant articles and documents
ETUDE DE NOUVELLES REACTIONS PAR TRANSFERT MONOELECTRONIQUE: ACTION D'ORGANOGERMYLLITHIUMS SUR LE FURFURAL, LE THIOPHENALDEHYDE ET LES DERIVES NITRES CORRESPONDANTS
Riviere, P.,Castel, A.,Cosledan, F.
, p. 169 - 180 (2007/10/02)
The organogermyllithiums R3GeLi (R=Ph, Mes) were treated with several carbonyl conjugated substrates (2-furaldehyde, 2-thiophenecarboxaldehyde and their nitro-corresponding compounds).Only the germylation reactions of carbonyl group have been observed with a regioselectivity depending on the nature of the insaturated cycle.With 2-furaldehyde and 2-thiophenecarboxaldehyde, the germylcarbinols 1 are mainly obtained by C-germylation reaction.When an excess of aldehyde was used, the formation of germylketone 2 is surprisingly observed.With nitro compounds, the O-germylation reaction is preponderant.In this case, a single electron transfer mechanism takes place and was confirmed by ESR study.We observed the corresponding organic radical anion.The hyperfine structure of which has been resolved.Key words: SET reactions, germylation, radical anion, germyllithiums, germylketones, germanium centered radical.