80885-62-7Relevant academic research and scientific papers
Importance of Structure of α,β-Ethylenic Ketones during Their Reductive Coupling Promoted by the TiCl4-Mg Reagent
Pons, Jean-Marc,Santelli, Maurice
, p. 877 - 884 (2007/10/02)
In most cases, the reductive coupling of α,β-ethylenic ketones by the TiCl4-Mg reagent leads to 1,3,5-trienes and bisallylic pinacols.Some α,β-enones of s-cis configuration, such as (+)-pulegone, show a particular reactivity: formation of dihydro ketones in the presence of tert-butyl alcohol and reductive alkylation with allylic halides or benzyl bromide.Results are accordance with a polymeric structure for the native low-valent titanium species, and in the case of some s-cis-enones, they can be explained by the intervention of a oxametallacyclopentene.
REDUCTIVE COUPLING OF α,β-ENONES I : REDUCTION OF METHYL-VINYL KETONE AND MESITYL OXIDE.
Pons, Jean-Marc,Zahra, Jean-Pierre,Santelli, Maurice
, p. 3965 - 3968 (2007/10/02)
Reductive coupling of methyl-vinyl ketone with TiCl4-Mg gives pinacol 1 (25percent).According to the reducing agents, mesityl oxide yields 2,4,5,7-tetramethyl-octa-2,4,6-triene 3 (with 4TiCl3-LiAlH4), triene 3 or 2,4,5,7-tetramethyl-octa-2,6-dien-4,5-diol 5 (with TiCl4-Mg), pinacol 5 (with VCl3-Mg), and 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentene 7 (with CrCl3-Mg or FeCl3-Mg or ZrCl4-Mg) as major products.
