Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid
Patrícia S. M. Amado
1, 2, 3
,
Luı́s M.T Frija
4
,
Jaime B. Coelho
5
,
Paul O'Neill
3
,
Maria L. S. Cristiano
1, 2
Publication type: Journal Article
Publication date: 2021-07-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34279102
Organic Chemistry
Abstract
A novel protocol for the preparation of non-symmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes, promoted by the heterogeneous silica sulfuric acid (SSA) catalyst, is reported. Different ketones react under mild conditions with gem-dihydroperoxides or peroxysilyl alcohols/β-hydroperoxy alcohols to generate the corresponding endoperoxides in good yields. Our mechanistic proposal, assisted by molecular orbital calculations, at the ωB97XD/def2-TZVPP/PCM(DCM)//B3LYP/6-31G(d) level of theory, enhances the role of SSA in the cyclocondensation step. This novel procedure differs from previously reported methods by using readily available and inexpensive reagents, with recyclable properties, thereby establishing a valid alternative approach for the synthesis of new biologically active endoperoxides.
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16
Total citations:
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Citations from 2024:
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(43.75%)
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Amado P. S. M. et al. Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid // Journal of Organic Chemistry. 2021. Vol. 86. No. 15. pp. 10608-10620.
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Amado P. S. M., Frija L. M., Coelho J. B., O'Neill P., Cristiano M. L. S. Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid // Journal of Organic Chemistry. 2021. Vol. 86. No. 15. pp. 10608-10620.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.1c01258
UR - https://doi.org/10.1021/acs.joc.1c01258
TI - Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid
T2 - Journal of Organic Chemistry
AU - Amado, Patrícia S. M.
AU - Frija, Luı́s M.T
AU - Coelho, Jaime B.
AU - O'Neill, Paul
AU - Cristiano, Maria L. S.
PY - 2021
DA - 2021/07/19
PB - American Chemical Society (ACS)
SP - 10608-10620
IS - 15
VL - 86
PMID - 34279102
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2021_Amado,
author = {Patrícia S. M. Amado and Luı́s M.T Frija and Jaime B. Coelho and Paul O'Neill and Maria L. S. Cristiano},
title = {Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.1c01258},
number = {15},
pages = {10608--10620},
doi = {10.1021/acs.joc.1c01258}
}
Cite this
MLA
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Amado, Patrícia S. M., et al. “Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid.” Journal of Organic Chemistry, vol. 86, no. 15, Jul. 2021, pp. 10608-10620. https://doi.org/10.1021/acs.joc.1c01258.