54568-51-3Relevant academic research and scientific papers
The Photocyclization of N,N-Dialkyl β-Oxo Amides Adsorbed on Silica Gel
Hasegawa, Tadashi,Moribe, Jun-ichi,Yoshioka, Michikazu
, p. 1437 - 1439 (2007/10/02)
β-Oxo amides 1 adsorbed on silica gel underwent photocyclization via δ-hydrogen abstraction to give the five membered lactams 2.No severe restrictions on the molecular motion could be observed in the photoreaction on the silica-surface.However, the relati
Photochemical Reaction of α-Alkyl-β-oxoamides. Competitive γ- and δ-Hydrogen Abstraction by Excited Ketone Carbonyl Groups
Hasegawa, Tadashi,Arata, Yoshiaki,Mizuno, Kouichi,Masuda, Kenji,Yoshihara, Nobutoshi
, p. 541 - 544 (2007/10/02)
The α-alkyl-β-oxoamides (1a-i) undergo the Norrish Type II photoreaction.The excited ketone carbonyl group in the β-oxoamides (1c, 1f-i) abstracts γ- and δ-hydrogen competitively from the n,?* triplet state.The regioselectivity of the hydrogen abstraction is affected by both the γ- and the δ-substituents.The presence of γ- or δ-substitution increases the γ- or the δ-hydrogen abstraction, respectively.The δ-hydrogen abstraction greatly predominates over the γ-hydrogen absraction in the photolyses of the α-ethyl-β-oxoamides (1f) and (1i).
