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Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde

Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
, 
Artur R Tagirov 1
Artur R Tagirov
, 
Shamil Mubarakovich Salikhov 1
Shamil Mubarakovich Salikhov
, 
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
1 Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2023.01.002
Published 2022-12-26
Communication , Volume 33, Issue 1, 9-10
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Faizullina L. K. et al. Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 9-10.
GOST all authors (up to 50) Copy
Faizullina L. K., Tagirov A. R., Salikhov S. M., Valeev F. A. Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 9-10.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.002
TI - Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde
T2 - Mendeleev Communications
AU - Faizullina, Liliya Khalitovna
AU - Tagirov, Artur R
AU - Salikhov, Shamil Mubarakovich
AU - Valeev, Farid Abdullovich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 9-10
IS - 1
VL - 33
ER -
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@article{2022_Faizullina,
author = {Liliya Khalitovna Faizullina and Artur R Tagirov and Shamil Mubarakovich Salikhov and Farid Abdullovich Valeev},
title = {Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.002},
number = {1},
pages = {9--10},
doi = {10.1016/j.mencom.2023.01.002}
}
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Faizullina, Liliya Khalitovna, et al. “Ene reaction of Diels-Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 9-10. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.002.
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Keywords

acetaldehyde
Diels–Alder adduct
ene reaction
ketals
levoglucosenone
Lewis acids
oxetanes.

Abstract

Diels-Alder adducts of levoglucosenone with isoprene, butadiene and piperylene in the presence of AlCl3 smoothly react with acetaldehyde or benzaldehyde to give products of the ene reaction, the hydroxy group of the primary intermediates participating in the formation of semiketal moiety. The yields of the reaction products depend both on the Lewis acid used (AlCl , BF ·Et O, ZnBr , SnCl or EtAlCl2) and on the nature of the substrate.

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