Abstract:
Photolysis of 5,6-epoxy 4-keto derivatives of the Diels–Alder adduct of levoglucosenone and piperylene in C6H6–MeOH causes cleavage of the C4–C5 bond giving product containing vicinal acetone and alkyl acetate moieties, the latter would further transform into 1-alkoxycarbonyl-2-hydroxy-2-methylcyclopentane derivative annulated to 5,8-dioxabicyclo[3.2.1]octane cage.
Citation:
I. M. Biktagirov, L. Kh. Faizullina, Sh. M. Salikhov, F. Z. Galin, F. A. Valeev, “Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene”, Mendeleev Commun., 27:3 (2017), 237–239
Linking options:
https://www.mathnet.ru/eng/mendc1953
https://www.mathnet.ru/eng/mendc/v27/i3/p237
This publication is cited in the following 2 articles:
L. Kh. Faizullina, Yu. S. Galimova, M. Yu. Ovchinnikov, Sh. M. Salikhov, S. L. Khursan, F. A. Valeev, “Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones”, Mendeleev Commun., 29:1 (2019), 64–66
L. Kh. Faizullina, Yu. S. Galimova, Yu. A. Khalilova, Sh. M. Salikhov, F. A. Valeev, “Aldol-type transformations of levoglucosenone-derived medium-sized keto lactones”, Mendeleev Commun., 28:5 (2018), 482–484
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