2547-28-6Relevant academic research and scientific papers
STUDIES ON THE STEREOCHEMISTRY OF REDUCTION REACTIONS ON 10-R SUBSTITUTED trans DECAL-2-ONES
Maio, Giorgio Di,Migneco, Luisa M.,Vecchi, Elisabetta
, p. 6053 - 6060 (2007/10/02)
Relative rates kax and keq of reduction reactions of the title compounds (R=H, Me, CO2Et, Cl) have been measured in three different reaction conditions (LiAlH4, LiEt3BH, NaBH4).We found that keq decreases as the substituent electronegativity increases when lithium reactants are used and that kax increases as the substituent electronegativity increases when sodium reactant is used.The synthesis of trans and cis 10-chloro-decal-2-ones is also described.
Stereoselectivity in the Formation and Allylic Rearrangement of 8a-Methyl- and 8a-Ethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalenyl Hydroperoxides
Avila, David V.,Davies, Alwyn G.,Davison, Ian G. E.
, p. 1847 - 1852 (2007/10/02)
4a-Methyl- and 4a-ethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene have been subjected to singlet oxygen oxygenation, and the various hydroperoxides which are formed have been characterised.Evidence is presented that the 8aβ-alkyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4aα-yl hydroperoxides (I; R=Me or Et) rearrange suprafacially and irreversibly in chloroform at 25 deg C to give only the 4aβ-alkyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2α-yl hydroperoxides (II).Under the same conditions, the corresponding 8aβ-alkyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4aβ-yl hydroperoxides rearrange much more slowly.
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.
