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Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones

Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
, 
Yuliya Sergeevna Galimova 1
Yuliya Sergeevna Galimova
,  , 
Shamil Mubarakovich Salikhov 1
Shamil Mubarakovich Salikhov
, 
Sergei Leonidovich Khursan 1
Sergei Leonidovich Khursan
, 
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
10.1016/j.mencom.2019.01.021
Published 2018-12-28
Communication , Volume 29, Issue 1, 64-66
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Faizullina L. K. et al. Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 64-66.
GOST all authors (up to 50) Copy
Faizullina L. K., Galimova Y. S., Ovchinnikov M. Y., Salikhov S. M., Khursan S. L., Valeev F. A. Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 64-66.
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TY - JOUR
DO - 10.1016/j.mencom.2019.01.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.021
TI - Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones
T2 - Mendeleev Communications
AU - Faizullina, Liliya Khalitovna
AU - Galimova, Yuliya Sergeevna
AU - Ovchinnikov, Mikhail Yur'evich
AU - Salikhov, Shamil Mubarakovich
AU - Khursan, Sergei Leonidovich
AU - Valeev, Farid Abdullovich
PY - 2018
DA - 2018/12/28
PB - Mendeleev Communications
SP - 64-66
IS - 1
VL - 29
ER -
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@article{2018_Faizullina,
author = {Liliya Khalitovna Faizullina and Yuliya Sergeevna Galimova and Mikhail Yur'evich Ovchinnikov and Shamil Mubarakovich Salikhov and Sergei Leonidovich Khursan and Farid Abdullovich Valeev},
title = {Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.021},
number = {1},
pages = {64--66},
doi = {10.1016/j.mencom.2019.01.021}
}
MLA
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Faizullina, Liliya Khalitovna, et al. “Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones.” Mendeleev Communications, vol. 29, no. 1, Dec. 2018, pp. 64-66. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.021.

Abstract

Levoglucosenone-derived 2-[(2S,3S,6S)-2-hydroxymethyl-5,5,6-trimethoxytetrahydro-2H-pyran-3-ylcarbonyl]cyclo-pentanone upon boiling in benzene in the presence of NaH undergoes the retro-Dieckmann-type reaction to afford 10-membered lactone, while storing this reaction mixture at room temperature brings about the starting cyclopentanone derivative. Several structurally analogous compounds were examined in respect of similar transformations.

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