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Issue 0, 1987

Photochemical reactions of nitrile compounds. Part 2. Photochemistry of an α,β-unsaturated γ,δ-epoxy nitrile and an γ,δ-cyclopropyl nitrile

Abstract

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)isomerization 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-unsaturated γ,δ-cyclopropyl nitrile (4) afforded (38) as the main product along with (39) whereas, on triplet excitation of (4)(E/Z)-isomerization was the main process observed. Acid-catalysed rearrangements of compounds (1) and (8) were also studied.

Article information


J. Chem. Soc., Perkin Trans. 1, 1987, 1937-1944
Article type
Paper

Photochemical reactions of nitrile compounds. Part 2. Photochemistry of an α,β-unsaturated γ,δ-epoxy nitrile and an γ,δ-cyclopropyl nitrile

K. Ishii, M. Abe and M. Sakamoto, J. Chem. Soc., Perkin Trans. 1, 1987, 1937 DOI: 10.1039/P19870001937

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