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Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene

Ilgiz Maratovich Biktagirov 1
Ilgiz Maratovich Biktagirov
Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
Shamil Mubarakovich Salikhov 1
Shamil Mubarakovich Salikhov
Fanur Zufarovich Galin 1
Fanur Zufarovich Galin
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
Published 2017-04-25
CommunicationVolume 27, Issue 3, 237-239
3
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Biktagirov I. M. et al. Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 237-239.
GOST all authors (up to 50) Copy
Biktagirov I. M., Faizullina L. K., Salikhov S. M., Galin F. Z., Valeev F. A. Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 237-239.
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TY - JOUR
DO - 10.1016/j.mencom.2017.05.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.006
TI - Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene
T2 - Mendeleev Communications
AU - Biktagirov, Ilgiz Maratovich
AU - Faizullina, Liliya Khalitovna
AU - Salikhov, Shamil Mubarakovich
AU - Galin, Fanur Zufarovich
AU - Valeev, Farid Abdullovich
PY - 2017
DA - 2017/04/25
PB - Mendeleev Communications
SP - 237-239
IS - 3
VL - 27
ER -
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@article{2017_Biktagirov,
author = {Ilgiz Maratovich Biktagirov and Liliya Khalitovna Faizullina and Shamil Mubarakovich Salikhov and Fanur Zufarovich Galin and Farid Abdullovich Valeev},
title = {Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.006},
number = {3},
pages = {237--239},
doi = {10.1016/j.mencom.2017.05.006}
}
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Biktagirov, Ilgiz Maratovich, et al. “Photochemical rearrangement of 5,6-epoxy derivatives of the Diels–Alder adduct of levoglucosenone and piperylene.” Mendeleev Communications, vol. 27, no. 3, Apr. 2017, pp. 237-239. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.006.

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.

References

1.
Cycloaddition and one-carbon homologation studies in the synthesis of advanced iridoid precursors
Stevens A.T., Caira M.R., Bull J.R., Chibale K.
Organic and Biomolecular Chemistry, 2009
2.
Regiocontrolled dieckmann condensation of 3,4-Bis(methoxycarbonylmethyl) levoglucosenone derivative
Iskakova M.M., Biktagirov I.M., Faizullina L.K., Salikhov S.M., Safarov M.G., Valeev F.A.
Russian Journal of Organic Chemistry, 2014
3.
Transformation of the cyclohexene fragment in the Diels-Alder adducts of levoglucosenone with 1,3-dienes into cyclopentane
Biktagirov I.M., Faizullina L.K., Salikhov S.M., Safarov M.G., Valeev F.A.
Russian Journal of Organic Chemistry, 2015
4.
Oxidation with CrO3·2Py of levoglucosenone and 1,3-dienes Diels-Alder adducts
Biktagirov I.M., Faizullina L.K., Salikhov S.M., Galin F.Z., Safarov M.G., Valeev F.A.
Russian Journal of Organic Chemistry, 2016
5.
Contraction of the cyclohexene ring in the Diels–Alder adduct of levoglucosenone with piperylene
Biktagirov I.M., Faizullina L.K., Salikhov S.M., Valeev F.A.
Russian Journal of Organic Chemistry, 2016
7.
Photochemical rearrangements of 2-cyclohexenones
Chapman O.L., Rettig T.A., Griswold A.A., Dutton A.I., Fitton P.
Tetrahedron Letters, 1963
9.
10.1016/j.mencom.2017.05.006_sbref0025a
Padwa
1967
14.
Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines
Hasegawa E., Ishiyama K., Horaguchi T., Shimizu T.
Journal of Organic Chemistry, 1991
16.
5-METHYL-5-HEXEN-2-ONE
17.
Intramolecular aldol condensation of michael adducts of levoglucosenone and methylketo-β-carbonyl compounds
Doronina O.Y., Khalilova Y.A., Sharipov B.T., Spirikhin L.V., Valeev F.A.
Russian Journal of Organic Chemistry, 2012