158392-63-3Relevant academic research and scientific papers
Zinc-mediated C-C bond sigmatropic rearrangement: A new and efficient methodology for the synthesis of β-diketones
Li, Lezhen,Cai, Peijie,Xu, Da,Guo, Qingxiang,Xue, Song
, p. 8131 - 8134 (2007)
(Chemical Equation Presented) A new and efficient methodology has been developed for the synthesis of β-diketones from aromatic α-bromo ketones in the presence of Furukawa reagent under mild conditions. The present transformation is proposed to proceed via a Reformatsky-type reaction of α-bromo ketones, followed by C-C bond sigmatropic rearrangement of the aldolate intermediate to give β-diketones in moderate to good isolated yields, while aliphatic α-bromomethyl ketones resulted in the formation of 2,4-disubstituted furans or cis-1,2-disubstituted cyclopropanols in moderate yields. The scope of this process was investigated, and a tentative mechanism was proposed.
One step preparation of 1,4-diketones from methyl ketones and α-bromomethyl ketones in the presence of ZnCl2·t-BuOH·Et2NR as a condensation agent
Nevar,Kel'in,Kulinkovich
, p. 1259 - 1262 (2007/10/03)
1,4-Diketones have been prepared in one step from methyl ketones and α-bromomethyl ketones under the action of ZnCl2·t-BuOH·Et2NR as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction is proposed to go through aldol condensation of ketones followed by 1,3-dehydro-bromination of aldol products and cleavage of activated cyclopropyl intermediates.
A new simple synthesis of aryl-substituted 1,4-diketones
Kel'in, Alexander V.,Kulinkovich, Oleg G.
, p. 330 - 332 (2007/10/03)
1,4-Diketones have been prepared by aldol condensation of methyl ketones with α-bromo ketones in the presence of tert-butoxymagnesium or diethylamido magnesium bromide and subsequent rearrangement of the formed 4-bromo-3-hydroxy ketones under the action o
NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward α-Halo Ketone or α-Halo Imine
Yasuda, Makoto,Katoh, Yasuhiro,Shibata, Ikuya,Baba, Akio,Matsuda, Haruo,Sonoda, Noboru
, p. 4386 - 4392 (2007/10/02)
NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the 119Sn NMR spectrum and increased coupling constants J(119Sn-13C), compared wit
SYNTHESIS OF 1,4-DIKETONES, 3,4-EPOXY KETONES, AND 2,4-DISUBSTITUTED FURANS BASED ON THE PRODUCTS FROM CONDENSATION OF THE MAGNESIUM ENOLATES OF KETONES WITH α-BROMO KETONES
Kel'in, A. V.,Kulinkovich, O. G.
, p. 202 - 206 (2007/10/02)
4-Bromo-3-hydroxy ketones were obtained by the condensation of methyl ketones with 2-bromo ketones in the presence of tert-butoxymagnesium bromide or by the action of organomagnesium compounds on 2-bromo ketones.The reaction of 4-bromo-3-hydroxy ketones w
