144467-12-9Relevant articles and documents
Access to 2-Amino-3-Arylthiophenes by Base-Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur
Nguyen, Thi Thu Tram,Le, Van Anh,Retailleau, Pascal,Nguyen, Thanh Binh
supporting information, p. 160 - 165 (2019/12/11)
A straightforward access to 2-amino-3-arylthiophenes has been developed via one-pot two-step three-component reaction of arylacetonitriles, chalcones and elemental sulfur. The first step consists of a DBU-catalyzed formation of Michael adduct between aryl
Reaction of metalated nitriles with enones
Reich, Hans J.,Biddle, Margaret M.,Edmonston, Robert J.
, p. 3375 - 3382 (2007/10/03)
(Chemical Equation Presented) There have been a number of reports of the kinetic conjugate (1,4) addition of metalated arylacetonitriles to enones. Several proposals have been made to explain this behavior based on nucleophile structure or aggregation state or on the HSAB properties of the reactants. A reexamination of these studies showed that in each case the 1,4 adducts resulted from equilibration of the kinetically formed 1,2 adducts to the more stable 1,4 adducts. Thus, no conclusions about the origins of 1,4 selectivity can be drawn from these experiments. The 1,2 addition, retro-1,2 addition, 1,4 addition, and retro-1,4 addition of lithiophenylacetonitrile to benzylideneacetone were examined, and a free energy level diagram was constructed for the reaction.
Effect of aggregation of nitrile anions on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone
Strzalko,Seyden-Penne,Wartski,Froment,Corset
, p. 3935 - 3936 (2007/10/02)
A direct evidence of the influence of aggregation state of lithiated penylacetonitrile 1 on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone 2 was established. Progressive addition of hexane to THF solutions raised the aggregates proportion of 1 as evidenced by IR ν(CN) band and led to an increase of 1,4 adduct. Monomers afforded 1,2 addition in pure THF.