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Reactions of cyrene with formaldehyde

Yuliya Aleksandrovna Khalilova 1
Yuliya Aleksandrovna Khalilova
, 
Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
, 
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.2023.09.019
Published 2023-09-01
Communication , Volume 33, Issue 5, 648-649
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Khalilova Y. A. et al. Reactions of cyrene with formaldehyde // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 648-649.
GOST all authors (up to 50) Copy
Khalilova Y. A., Faizullina L. K., Salikhov S. M., Valeev F. A. Reactions of cyrene with formaldehyde // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 648-649.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.019
TI - Reactions of cyrene with formaldehyde
T2 - Mendeleev Communications
AU - Khalilova, Yuliya Aleksandrovna
AU - Faizullina, Liliya Khalitovna
AU - Salikhov, Shamil Mubarakovich
AU - Valeev, Farid Abdullovich
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 648-649
IS - 5
VL - 33
ER -
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@article{2023_Khalilova,
author = {Yuliya Aleksandrovna Khalilova and Liliya Khalitovna Faizullina and Shamil Mubarakovich Salikhov and Farid Abdullovich Valeev},
title = {Reactions of cyrene with formaldehyde},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.019},
number = {5},
pages = {648--649},
doi = {10.1016/j.mencom.2023.09.019}
}
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Khalilova, Yuliya Aleksandrovna, et al. “Reactions of cyrene with formaldehyde.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 648-649. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.019.

Keywords

chiral dioxane
cyrene
diol.
enolization
formaldehyde
levoglucosenone

Abstract

Cyrene reacts with 35% aqueous formaldehyde in the presence of K2CO3, tetramethylguanidine and Et3N to give three products, viz., major α,α-bis(hydroxymethyl) derivative, a product of its keto group reduction, and 3,5,11,12-tetraoxatricyclo[7.2.1.02,7]dodecan-2-ol. The options for the derivatization of the hydroxy groups with benzyl, tosyl, isopropylidene, and methylene acetal protecting groups were studied.

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