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On the Photochemical Dimerization of Some 5-Substituted 2-Styryl-4-pyrones. The Effect of 5-Hydroxy-/5-Methoxy- Substitution (CROSBI ID 93200)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Stiplošek, Zdenka ; Šindler-Kulyk, Marija ; Jakopčić, Krešimir ; Višnjevac, Aleksandar ; Kojić-Prodić, Biserka On the Photochemical Dimerization of Some 5-Substituted 2-Styryl-4-pyrones. The Effect of 5-Hydroxy-/5-Methoxy- Substitution // Journal of heterocyclic chemistry, 39 (2002), 1; 37-44-x

Podaci o odgovornosti

Stiplošek, Zdenka ; Šindler-Kulyk, Marija ; Jakopčić, Krešimir ; Višnjevac, Aleksandar ; Kojić-Prodić, Biserka

engleski

On the Photochemical Dimerization of Some 5-Substituted 2-Styryl-4-pyrones. The Effect of 5-Hydroxy-/5-Methoxy- Substitution

Irradiation of styryl-4-pyrones 1a-1d or 2a-2e (6-9x10-3 M, methanol solution) with filtered (RAYONET photochemical reactor, 300 nm) or unfiltered uv-light (high-pressure mercury arc lamp) under aerobic conditions led mainly to dimeric products. Parent 5-hydroxy-substituted compounds 1a-1d yielded exclusively "half-cage" dimers 3a-d characteristic for 4-pyrone dimerization. 5-Methoxy-analogues 2a-2e behave like typical stilbene structures and the mixtures of tetrasubstituted cyclobutanes 4 and 5 accompanied with minor amount of phenantrene-like compound 6 were the only isolable products of the irradiation. The structure elucidation of products is based on spectral data obtained from MS, IR, 1H NMR and 13C NMR spectra applying COSY, APT, HETCOR, HMBC and NOESY techniques.

dimerization; photochemical; 4-pyrone; benzo[f]chromone; styrylpyrone; photocycloaddition; photodehydrocyclization; substituent effect

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Podaci o izdanju

39 (1)

2002.

37-44-x

objavljeno

0022-152X

Povezanost rada

Kemija

Indeksiranost