22292-84-8Relevant academic research and scientific papers
KHSO4 assisted Michael addition-elimination reactions of formylated acetophenones in water: A facile general green synthetic route to 3-(alkyl/aralkyl/aryl)amino-1-arylprop-2-en-1-ones
Devi,Dutta,Nongkhlaw,Vishwakarma
, p. 739 - 742 (2011/08/09)
A facile general green synthetic route to 3-(alkyl/aralkyl/aryl)amino-1- arylprop-2-en-1-ones in excellent yields has been developed by reacting formylated acetophenones with primary amines assisted by KHSO4 in water.
Deuterium isotope effects on 13C chemical shifts of enaminones
Zheglova, Donka Kh.,Genov, Daniel G.,Bolvig, Simon,Hansen, Poul Erik
, p. 1016 - 1023 (2007/10/03)
Deuterium isotope effects on 13C chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, 2δC-1 (ND). Methyl-substitution at C-1 leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between 2δC-1(ND) and 3δC-2′(ND). The latter becomes negative in the sterically hindered cases. 3δC-2′(ND) may therefore be used as a gauge of the twist of the phenyl ring. o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller 2δC-2(ND) and 2δC-2″(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer 2δC(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, 2δC(OD), isotope effects. Acta Chemica Scandinavica 1997.
