39879-90-8Relevant academic research and scientific papers
BOROHYDRIDE REDUCTION OF Δ1,9 2-OCTALONE : CATION INFLUENCE AND AMINE ADDITION EFFECTS
D'Incan, E.,Loupy, A.,Maia, A.
, p. 941 - 944 (1981)
Proton removal of Δ1,9 2-octalone occurs when reacted with NBu4BH4 in aprotic solvents while 1-2 reduction is important with NaBH4 in THF.Both are inhibited when NaBH4 reduction is performed in the presence of amines, leading thus to highly selective formation of saturated alcohols.
SELECTIVITE DE LA REDUCTION D'α-ENONES POLYCYCLIQUES PAR LES BOROHYDRURES: EFFET DE L'ADDITION DE TETRAMETHYL-ETHYLENEDIAMINE AU BOROHYDRURE DE TETRABUTYLAMMONIUM
D'incan, E.,Loupy, A.,Maia, A.,Seyden-Penne, J.,Viout, P.
, p. 2923 - 2927 (2007/10/02)
Δ1,9octalone, Δ1,9-10-methyl octalone and testosterone were reduced by NBu4BH4, alone or in the presence of tetramethylethylenediamine (TMEDA), in THF and in toluene.With TMEDA, the first step of the reduction is the regioselective 1,4 attack by BH4(1-) which leads either to the saturated ketones or to the corresponding saturated alcohols.The results observed under different conditions were interpreted by the intervention of various reductive species: diborane, enoxyborohydrides in the absence of TMEDA, amine-borane in its presence.
