99557-57-0Relevant academic research and scientific papers
Photoreactions of α,β-Unsaturated γ,δ-Epoxy Nitriles with Amines. The Novel Photoadditions of Tertiary Amines to the α-Position of the Nitriles
Ishii, Keitaro,Kotera, Masashi,Sakamoto, Masanori
, p. 2465 - 2466 (1994)
Direct irradiation of α,β-unsaturated γ,δ-epoxy nitriles (e.g. 1) and tertiary amines gives rise to a novel 1:1 α-addition and subsequent retro-Michael reaction leading to α-alkylidenenitriles (e.g. 2).
Novel photoadditions of tertiary amines to the α-position of α,β-unsaturated γ,δ-epoxy nitriles
Ishii, Keitaro,Hakamada, Satoshi,Nagano, Mayumi,Noji, Masahiro,Sugiyama, Shigeo,Kotera, Masashi,Sakamoto, Masanori
, p. 1592 - 1598 (2007/10/03)
The photoreactions of α,β-unsaturated γ,δ-epoxy nitriles 1,2,13 and 16 with triethylamine give rise to novel 1:1 α-adducts (e.g.,5) efficiently. After treatment with silica gel, the adducts undergo retro-Michael reaction leading to the corresponding α-alk
PHOTOCHEMICAL REACTIONS OF NITRILE COMPOUNDS. PART 2. 1PHOTOCHEMISTRY OF AN α,β-UNSATURATED γ,δ-EPOXY NITRILE AND γ,δ-CYCLOPROPYL NITRILE
Ishii, Keitaro,Abe, Masao,Sakamoto, Masanori
, p. 1937 - 1944 (2007/10/02)
Direct irradiation (λ 254 nm) of the α,β-unsaturated γ,δ-epoxy nitrile (1) led selectively to the products (13)-(19) arising from a carbonyl ylide or a carbene intermediate.However, products of an (E/Z)-isomerisation and a transformation via C(γ)-O bond cleavage of the oxirane, which are triplet processes, were not observed.On singlet excitation ( λ 254 nm), the α,β-unsaterated γ,δ-cyclopropyl nitrile (4) afforded (38) as the main product along with (39) whereas, on triplet excitation of (4) (E/Z)-isomerisation was the main process observed.Acid-catalysed rearrangements of compounds (1) and (8) were also studied.
